CN105218322A - A kind of synthetic method of 3,5-dimethoxybenzoic acid ethyl ester - Google Patents

A kind of synthetic method of 3,5-dimethoxybenzoic acid ethyl ester Download PDF

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CN105218322A
CN105218322A CN201510722005.XA CN201510722005A CN105218322A CN 105218322 A CN105218322 A CN 105218322A CN 201510722005 A CN201510722005 A CN 201510722005A CN 105218322 A CN105218322 A CN 105218322A
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dimethoxybenzoic acid
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丁玉琴
王志慧
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/60—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by oxidation reactions introducing directly hydroxy groups on a =CH-group belonging to a six-membered aromatic ring with the aid of other oxidants than molecular oxygen or their mixtures with molecular oxygen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/15—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
    • C07C67/11—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups

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Abstract

The invention discloses a kind of synthetic method of 3,5-dimethoxybenzoic acid ethyl ester, belong to the field of chemical synthesis.The present invention first produces Resorcinol under given conditions with benzene, with Anhydrous potassium carbonate and carbonic acid gas under dimethyl formamide is solvent, pass through removal of impurities, decolouring, adjust ph, crystallisation by cooling finally obtains 3, 5-resorcylic acid, mix under the condition stirred with methyl-sulfate again, drip aqueous sodium hydroxide solution wherein to reflux, adjust ph after backflow, be cooled to 0 DEG C of filtration under diminished pressure, washing, drying obtains 3, 5-dimethoxybenzoic acid, last and dehydrated alcohol carries out esterification under the condition of the vitriol oil, final 3, 5-dimethoxybenzoic acid ethyl ester.

Description

A kind of synthetic method of 3,5-dimethoxybenzoic acid ethyl ester
Technical field
The invention discloses a kind of synthetic method of 3,5-dimethoxybenzoic acid ethyl ester, belong to the field of chemical synthesis.
Background technology
2,6-dimethoxybenzoic acid is the intermediate preparing serial acylphosphine oxide.Acylphosphine oxide photoinitiator has the features such as high initiating activity, photobleaching, the rear product not yellowing of solidification, good thermostability and resistance to hydrolysis in near-ultraviolet light district, be particularly suitable for the light trigger being used as thick-layer, coloured and white photoactive coating.It can also be used for the aspects such as imaging press plate, photic etching reagent, photo-cured coating, optical fiber coatings, embossment press plate in addition.
Up to now, see bibliographical information to prepare 2,6-dimethoxybenzoic acid and have two kinds of synthetic routes: take Resorcinol as raw material, with phenyl-dihalide formic acid for raw material.Main raw material needed for rear a kind of synthetic route, 2,6-phenyl-dihalide formic acid is without commercial goods, and during preparation, reaction process is complicated, need synthesize, generally do not adopt through polystep reaction.Be that the synthetic route of raw material has two lines again with Resorcinol, one first introduces carboxyl, generates 2,6-DHBA, then methylate.Another kind first methylates, phenylene dimethyl ether between generation, then introduce carboxyl through organometallic compound.Two lines are compared, and Article 1 route directly introduces carboxyl, and synthesis step is few, are convenient to implement.The Article 2 route appearance time is shorter, but will could introduce carboxyl through a few step reaction, and operation easier is large, and step is many, and cost is high.
Summary of the invention
The invention provides the synthetic method of 3, the 5-dimethoxybenzoic acid ethyl esters that a kind of reaction conditions is gentle, yield is high.
For achieving the above object, the synthetic route of the present invention 3,5-dimethoxybenzoic acid ethyl ester is:
The building-up process of 3, the 5-dimethoxybenzoic acid ethyl esters that the present invention relates to comprises the following steps:
(1) first compound concentration is the N of 0.1 ~ 0.3g/mL 2o 5/ CH 2cl 2solution, getting 50 ~ 70mL joins in the there-necked flask of band cooling jacket, 0.5 ~ 0.8gZBS catalyzer is added in bottle, under the state stirred, the benzene constant pressure funnel of 100 ~ 120mL is dropped in bottle after being warming up to 70 ~ 75 DEG C, dropwise rear continuation stirring 20 ~ 30min, then add saturated sodium bicarbonate solution to wash, after washing, centrifugation obtains solid and is Resorcinol;
(2) count by weight, get 70 ~ 80 parts of Resorcinols, 5 ~ 10 parts of Anhydrous potassium carbonates and 15 ~ 20 parts of carbon dioxides respectively to join and be equipped with in the 10L autoclave of electric mixing device, add dimethyl formamide and make solvent, 10 ~ 12h is reacted under 100 ~ 180 DEG C and 110 ~ 120MPa, autoclave is cooled to 30 ~ 35 DEG C and release after reaction terminates, pour out material, filtered removal solids and obtain filtrate;
(3) filtrate is carried out underpressure distillation, steam dimethyl formamide, backward filtrate in add the water of 120 ~ 130mL, carry out stirring and make it to dissolve, the concentrated hydrochloric acid regulator solution pH value dripping massfraction 38 ~ 40% is wherein 4 ~ 5, filter and remove insolubles, in filtrate, add zinc powder decolouring, remove excessive zinc powder and unreacted Resorcinol, it is 1 that aqueous phase massfraction 40% concentrated hydrochloric acid is acidified to pH, crystallization at 0 DEG C afterwards, filters and obtains 3,5-resorcylic acid;
(4) 70 ~ 80g3 is got, 5-resorcylic acid joins and whipping appts is housed, thermometer, in the 1L four-hole bottle of constant pressure funnel and prolong, 150 ~ 160mL methyl-sulfate is added again in bottle, stir condition under by the aqueous sodium hydroxide solution of 200 ~ 250mL massfraction 20 ~ 30% with being added drop-wise in four-hole boiling flask, at 28 ~ 35 DEG C, 40 ~ 50min is placed after dripping off, then be warming up to 50 ~ 55 DEG C and continue reaction 40 ~ 50min under the condition stirred, carry out backflow 2 ~ 3h, 100 ~ 120mL massfraction 40 ~ 45% aqueous sodium hydroxide solution is added again in bottle, then backflow 4 ~ 6h is continued, being cooled to room temperature after backflow, to be acidified to pH with massfraction 40% concentrated hydrochloric acid be again 1, control to leave standstill 4 ~ 5h at 0 DEG C, filtration under diminished pressure, at 105 ~ 110 DEG C, 1.5 ~ 2h is dried after solid is washed 2 ~ 3 times with frozen water, obtain 3, 5-dimethoxybenzoic acid,
(5) by obtained above 3,5-dimethoxybenzoic acid solid joins in beaker, in cup, add solid-liquid mass ratio is that the dehydrated alcohol of 1:1 boils, slowly drip massfraction 90 ~ 92% vitriol oil wherein in boiling part, filter after boiling 20 ~ 30min and remove solid, after filtrate carrying out is cooled to 0 DEG C, suction filtration obtains solid, rinse with frozen water, at being placed on 80 ~ 85 DEG C after flushing, dry 2 ~ 3h, obtains 3,5-dimethoxybenzoic acid ethyl ester.
Specific embodiments
The building-up process of one 3, the 5-dimethoxybenzoic acid ethyl ester that the present invention relates to comprises the following steps:
First compound concentration is the N of 0.1 ~ 0.3g/mL 2o 5/ CH 2cl 2solution, getting 50 ~ 70mL joins in the there-necked flask of band cooling jacket, 0.5 ~ 0.8gZBS catalyzer is added in bottle, under the state stirred, the benzene constant pressure funnel of 100 ~ 120mL is dropped in bottle after being warming up to 70 ~ 75 DEG C, dropwise rear continuation stirring 20 ~ 30min, then add saturated sodium bicarbonate solution to wash, after washing, centrifugation obtains solid and is Resorcinol, count by weight, get 70 ~ 80 parts of Resorcinols, 5 ~ 10 parts of Anhydrous potassium carbonates and 15 ~ 20 parts of carbon dioxides respectively to join and be equipped with in the 10L autoclave of electric mixing device, add dimethyl formamide and make solvent, 10 ~ 12h is reacted under 100 ~ 180 DEG C and 110 ~ 120MPa, autoclave is cooled to 30 ~ 35 DEG C and release after reaction terminates, pour out material, filtered removal solids and obtain filtrate, filtrate is carried out underpressure distillation, steam dimethyl formamide, backward filtrate in add the water of 120 ~ 130mL, carry out stirring and make it to dissolve, the concentrated hydrochloric acid regulator solution pH value dripping massfraction 38 ~ 40% is wherein 4 ~ 5, filter and remove insolubles, in filtrate, add zinc powder decolouring, remove excessive zinc powder and unreacted Resorcinol, it is 1 that aqueous phase massfraction 40% concentrated hydrochloric acid is acidified to pH, crystallization at 0 DEG C afterwards, filters and obtains 3,5-resorcylic acid, get 70 ~ 80g3, 5-resorcylic acid joins and whipping appts is housed, thermometer, in the 1L four-hole bottle of constant pressure funnel and prolong, 150 ~ 160mL methyl-sulfate is added again in bottle, stir condition under by the aqueous sodium hydroxide solution of 200 ~ 250mL massfraction 20 ~ 30% with being added drop-wise in four-hole boiling flask, at 28 ~ 35 DEG C, 40 ~ 50min is placed after dripping off, then be warming up to 50 ~ 55 DEG C and continue reaction 40 ~ 50min under the condition stirred, carry out backflow 2 ~ 3h, 100 ~ 120mL massfraction 40 ~ 45% aqueous sodium hydroxide solution is added again in bottle, then backflow 4 ~ 6h is continued, being cooled to room temperature after backflow, to be acidified to pH with massfraction 40% concentrated hydrochloric acid be again 1, control to leave standstill 4 ~ 5h at 0 DEG C, filtration under diminished pressure, at 105 ~ 110 DEG C, 1.5 ~ 2h is dried after solid is washed 2 ~ 3 times with frozen water, obtain 3, 5-dimethoxybenzoic acid, by obtained above 3,5-dimethoxybenzoic acid solid joins in beaker, in cup, add solid-liquid mass ratio is that the dehydrated alcohol of 1:1 boils, slowly drip massfraction 90 ~ 92% vitriol oil wherein in boiling part, filter after boiling 20 ~ 30min and remove solid, after filtrate carrying out is cooled to 0 DEG C, suction filtration obtains solid, rinse with frozen water, at being placed on 80 ~ 85 DEG C after flushing, dry 2 ~ 3h, obtains 3,5-dimethoxybenzoic acid ethyl ester.
Example 1
First compound concentration is the N of 0.1g/mL 2o 5/ CH 2cl 2solution, getting 50mL joins in the there-necked flask of band cooling jacket, 0.5gZBS catalyzer is added in bottle, under the state stirred, the benzene constant pressure funnel of 100mL is dropped in bottle after being warming up to 70 DEG C, dropwise rear continuation and stir 20min, then add saturated sodium bicarbonate solution to wash, after washing, centrifugation obtains solid and is Resorcinol, count by weight, get 70 parts of Resorcinols, 10 parts of Anhydrous potassium carbonates and 20 parts of carbon dioxides respectively to join and be equipped with in the 10L autoclave of electric mixing device, add dimethyl formamide and make solvent, 10h is reacted under 100 DEG C and 110MPa, autoclave is cooled to 30 DEG C and release after reaction terminates, pour out material, filtered removal solids and obtain filtrate, filtrate is carried out underpressure distillation, steam dimethyl formamide, backward filtrate in add the water of 120mL, carry out stirring and make it to dissolve, the concentrated hydrochloric acid regulator solution pH value dripping massfraction 38% is wherein 4, filter and remove insolubles, in filtrate, add zinc powder decolouring, remove excessive zinc powder and unreacted Resorcinol, it is 1 that aqueous phase massfraction 40% concentrated hydrochloric acid is acidified to pH, crystallization at 0 DEG C afterwards, filters and obtains 3,5-resorcylic acid, get 70g3, 5-resorcylic acid joins and whipping appts is housed, thermometer, in the 1L four-hole bottle of constant pressure funnel and prolong, 150mL methyl-sulfate is added again in bottle, stir condition under by the aqueous sodium hydroxide solution of 200mL massfraction 20% with being added drop-wise in four-hole boiling flask, at 28 DEG C, 40min is placed after dripping off, then be warming up to 50 DEG C under the condition stirred, continue reaction 40min, carry out backflow 2h, 100mL massfraction 40% aqueous sodium hydroxide solution is added again in bottle, then backflow 4h is continued, being cooled to room temperature after backflow, to be acidified to pH with massfraction 40% concentrated hydrochloric acid be again 1, control to leave standstill 4h at 0 DEG C, filtration under diminished pressure, at 105 DEG C, 1.5h is dried after solid frozen water is washed 2 times, obtain 3, 5-dimethoxybenzoic acid, by obtained above 3,5-dimethoxybenzoic acid solid joins in beaker, in cup, add solid-liquid mass ratio is that the dehydrated alcohol of 1:1 boils, slowly drip massfraction 90% vitriol oil wherein in boiling part, filter after boiling 20min and remove solid, after filtrate carrying out is cooled to 0 DEG C, suction filtration obtains solid, rinse with frozen water, dry 2h at being placed on 80 DEG C after flushing, obtains 3,5-dimethoxybenzoic acid ethyl ester.
Example 2
First compound concentration is the N of 0.2g/mL 2o 5/ CH 2cl 2solution, getting 60mL joins in the there-necked flask of band cooling jacket, 0.7gZBS catalyzer is added in bottle, under the state stirred, the benzene constant pressure funnel of 110mL is dropped in bottle after being warming up to 73 DEG C, dropwise rear continuation and stir 25min, then add saturated sodium bicarbonate solution to wash, after washing, centrifugation obtains solid and is Resorcinol, count by weight, get 75 parts of Resorcinols, 5 parts of Anhydrous potassium carbonates and 20 parts of carbon dioxides respectively to join and be equipped with in the 10L autoclave of electric mixing device, add dimethyl formamide and make solvent, 11h is reacted under 150 DEG C and 115MPa, autoclave is cooled to 33 DEG C and release after reaction terminates, pour out material, filtered removal solids and obtain filtrate, filtrate is carried out underpressure distillation, steam dimethyl formamide, backward filtrate in add the water of 125mL, carry out stirring and make it to dissolve, the concentrated hydrochloric acid regulator solution pH value dripping massfraction 39% is wherein 4.5, filter and remove insolubles, in filtrate, add zinc powder decolouring, remove excessive zinc powder and unreacted Resorcinol, it is 1 that aqueous phase massfraction 40% concentrated hydrochloric acid is acidified to pH, crystallization at 0 DEG C afterwards, filters and obtains 3,5-resorcylic acid, get 75g3, 5-resorcylic acid joins and whipping appts is housed, thermometer, in the 1L four-hole bottle of constant pressure funnel and prolong, 155mL methyl-sulfate is added again in bottle, stir condition under by the aqueous sodium hydroxide solution of 225mL massfraction 25% with being added drop-wise in four-hole boiling flask, at 31 DEG C, 45min is placed after dripping off, then be warming up to 53 DEG C under the condition stirred, continue reaction 45min, carry out backflow 2.5h, 110mL massfraction 43% aqueous sodium hydroxide solution is added again in bottle, then backflow 5h is continued, being cooled to room temperature after backflow, to be acidified to pH with massfraction 40% concentrated hydrochloric acid be again 1, control to leave standstill 4.5h at 0 DEG C, filtration under diminished pressure, at 108 DEG C, 1.7h is dried after solid frozen water is washed 2 times, obtain 3, 5-dimethoxybenzoic acid, by obtained above 3,5-dimethoxybenzoic acid solid joins in beaker, in cup, add solid-liquid mass ratio is that the dehydrated alcohol of 1:1 boils, slowly drip massfraction 91% vitriol oil wherein in boiling part, filter after boiling 25min and remove solid, after filtrate carrying out is cooled to 0 DEG C, suction filtration obtains solid, rinse with frozen water, dry 2.5h at being placed on 83 DEG C after flushing, obtains 3,5-dimethoxybenzoic acid ethyl ester.
Example 3
First compound concentration is the N of 0.3g/mL 2o 5/ CH 2cl 2solution, getting 70mL joins in the there-necked flask of band cooling jacket, 0.8gZBS catalyzer is added in bottle, under the state stirred, the benzene constant pressure funnel of 120mL is dropped in bottle after being warming up to 75 DEG C, dropwise rear continuation and stir 30min, then add saturated sodium bicarbonate solution to wash, after washing, centrifugation obtains solid and is Resorcinol, count by weight, get 80 parts of Resorcinols, 5 parts of Anhydrous potassium carbonates and 20 parts of carbon dioxides respectively to join and be equipped with in the 10L autoclave of electric mixing device, add dimethyl formamide and make solvent, 12h is reacted under 180 DEG C and 120MPa, autoclave is cooled to 35 DEG C and release after reaction terminates, pour out material, filtered removal solids and obtain filtrate, filtrate is carried out underpressure distillation, steam dimethyl formamide, backward filtrate in add the water of 130mL, carry out stirring and make it to dissolve, the concentrated hydrochloric acid regulator solution pH value dripping massfraction 38 ~ 40% is wherein 5, filter and remove insolubles, in filtrate, add zinc powder decolouring, remove excessive zinc powder and unreacted Resorcinol, it is 1 that aqueous phase massfraction 40% concentrated hydrochloric acid is acidified to pH, crystallization at 0 DEG C afterwards, filters and obtains 3,5-resorcylic acid, get 80g3, 5-resorcylic acid joins and whipping appts is housed, thermometer, in the 1L four-hole bottle of constant pressure funnel and prolong, 160mL methyl-sulfate is added again in bottle, stir condition under by the aqueous sodium hydroxide solution of 250mL massfraction 30% with being added drop-wise in four-hole boiling flask, at 35 DEG C, 50min is placed after dripping off, then be warming up to 55 DEG C under the condition stirred, continue reaction 50min, carry out backflow 3h, 120mL massfraction 45% aqueous sodium hydroxide solution is added again in bottle, then backflow 6h is continued, being cooled to room temperature after backflow, to be acidified to pH with massfraction 40% concentrated hydrochloric acid be again 1, control to leave standstill 5h at 0 DEG C, filtration under diminished pressure, at 110 DEG C, 2h is dried after solid frozen water is washed 3 times, obtain 3, 5-dimethoxybenzoic acid, by obtained above 3,5-dimethoxybenzoic acid solid joins in beaker, in cup, add solid-liquid mass ratio is that the dehydrated alcohol of 1:1 boils, slowly drip massfraction 92% vitriol oil wherein in boiling part, filter after boiling 30min and remove solid, after filtrate carrying out is cooled to 0 DEG C, suction filtration obtains solid, rinse with frozen water, dry 3h at being placed on 85 DEG C after flushing, obtains 3,5-dimethoxybenzoic acid ethyl ester.

Claims (1)

1. the synthetic method of a dimethoxybenzoic acid ethyl ester, is characterized in that the synthesis of 3,5-dimethoxybenzoic acid ethyl ester:
(1) first compound concentration is the N of 0.1 ~ 0.3g/mL 2o 5/ CH 2cl 2solution, getting 50 ~ 70mL joins in the there-necked flask of band cooling jacket, 0.5 ~ 0.8gZBS catalyzer is added in bottle, under the state stirred, the benzene constant pressure funnel of 100 ~ 120mL is dropped in bottle after being warming up to 70 ~ 75 DEG C, dropwise rear continuation stirring 20 ~ 30min, then add saturated sodium bicarbonate solution to wash, after washing, centrifugation obtains solid and is Resorcinol;
(2) count by weight, get 70 ~ 80 parts of Resorcinols, 5 ~ 10 parts of Anhydrous potassium carbonates and 15 ~ 20 parts of carbon dioxides respectively to join and be equipped with in the 10L autoclave of electric mixing device, add dimethyl formamide and make solvent, 10 ~ 12h is reacted under 100 ~ 180 DEG C and 110 ~ 120MPa, autoclave is cooled to 30 ~ 35 DEG C and release after reaction terminates, pour out material, filtered removal solids and obtain filtrate;
(3) filtrate is carried out underpressure distillation, steam dimethyl formamide, backward filtrate in add the water of 120 ~ 130mL, carry out stirring and make it to dissolve, the concentrated hydrochloric acid regulator solution pH value dripping massfraction 38 ~ 40% is wherein 4 ~ 5, filter and remove insolubles, in filtrate, add zinc powder decolouring, remove excessive zinc powder and unreacted Resorcinol, it is 1 that aqueous phase massfraction 40% concentrated hydrochloric acid is acidified to pH, crystallization at 0 DEG C afterwards, filters and obtains 3,5-resorcylic acid;
(4) 70 ~ 80g3 is got, 5-resorcylic acid joins and whipping appts is housed, thermometer, in the 1L four-hole bottle of constant pressure funnel and prolong, 150 ~ 160mL methyl-sulfate is added again in bottle, stir condition under by the aqueous sodium hydroxide solution of 200 ~ 250mL massfraction 20 ~ 30% with being added drop-wise in four-hole boiling flask, at 28 ~ 35 DEG C, 40 ~ 50min is placed after dripping off, then be warming up to 50 ~ 55 DEG C and continue reaction 40 ~ 50min under the condition stirred, carry out backflow 2 ~ 3h, 100 ~ 120mL massfraction 40 ~ 45% aqueous sodium hydroxide solution is added again in bottle, then backflow 4 ~ 6h is continued, being cooled to room temperature after backflow, to be acidified to pH with massfraction 40% concentrated hydrochloric acid be again 1, control to leave standstill 4 ~ 5h at 0 DEG C, filtration under diminished pressure, at 105 ~ 110 DEG C, 1.5 ~ 2h is dried after solid is washed 2 ~ 3 times with frozen water, obtain 3, 5-dimethoxybenzoic acid,
(5) by obtained above 3,5-dimethoxybenzoic acid solid joins in beaker, in cup, add solid-liquid mass ratio is that the dehydrated alcohol of 1:1 boils, slowly drip massfraction 90 ~ 92% vitriol oil wherein in boiling part, filter after boiling 20 ~ 30min and remove solid, after filtrate carrying out is cooled to 0 DEG C, suction filtration obtains solid, rinse with frozen water, at being placed on 80 ~ 85 DEG C after flushing, dry 2 ~ 3h, obtains 3,5-dimethoxybenzoic acid ethyl ester.
CN201510722005.XA 2015-10-31 2015-10-31 A kind of synthetic method of 3,5-dimethoxybenzoic acid ethyl ester Pending CN105218322A (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20190300471A1 (en) * 2018-03-30 2019-10-03 Miami University Method for the synthesis and purification of aryl acid esters
US10968162B2 (en) * 2018-03-30 2021-04-06 Miami University Method for the synthesis and purification of aryl acid esters

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