IT1155794B - Opt. substd. benzyl alcohol and benzaldehyde prepn. - by reacting benzoic acid with ethyl or isobutyl chloroformate to give benzoyl-ethyl-carbonate, then catalytic hydrogenation and opt. oxidn. - Google Patents
Opt. substd. benzyl alcohol and benzaldehyde prepn. - by reacting benzoic acid with ethyl or isobutyl chloroformate to give benzoyl-ethyl-carbonate, then catalytic hydrogenation and opt. oxidn.Info
- Publication number
- IT1155794B IT1155794B IT4781178A IT4781178A IT1155794B IT 1155794 B IT1155794 B IT 1155794B IT 4781178 A IT4781178 A IT 4781178A IT 4781178 A IT4781178 A IT 4781178A IT 1155794 B IT1155794 B IT 1155794B
- Authority
- IT
- Italy
- Prior art keywords
- ethyl
- opt
- benzyl alcohol
- benzaldehyde
- benzoic acid
- Prior art date
Links
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 title abstract 12
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 title abstract 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title abstract 4
- 235000019445 benzyl alcohol Nutrition 0.000 title abstract 4
- 239000005711 Benzoic acid Substances 0.000 title abstract 2
- 235000010233 benzoic acid Nutrition 0.000 title abstract 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title abstract 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 title abstract 2
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 title 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 title 1
- OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 abstract 2
- 150000001299 aldehydes Chemical class 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 abstract 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 abstract 1
- 239000001828 Gelatine Substances 0.000 abstract 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 abstract 1
- -1 aromatic alcohols Chemical class 0.000 abstract 1
- 239000005018 casein Substances 0.000 abstract 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 abstract 1
- 235000021240 caseins Nutrition 0.000 abstract 1
- 229920002301 cellulose acetate Polymers 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 229930016911 cinnamic acid Natural products 0.000 abstract 1
- 235000013985 cinnamic acid Nutrition 0.000 abstract 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 1
- 239000000796 flavoring agent Substances 0.000 abstract 1
- 235000019634 flavors Nutrition 0.000 abstract 1
- 229920000159 gelatin Polymers 0.000 abstract 1
- 235000019322 gelatine Nutrition 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 abstract 1
- 229960001082 trimethoprim Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/298—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with manganese derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
Abstract
Prodn. of aromatic alcohols and aldehydes comprises (a) reaction of benzoic acid or its derivs. with isobutyl or ethyl-chloroformate, in the presence of an anhydrous base and an ahydrous, inert solvent, at 5-10 degrees C and atmospheric pressure, to obtain the corresp. mixed anhydride (b) catalytic hydrogenation of the mixed anhydride from (a) at 55-65 degrees C and 10.5-17.5kg/cm2 for 8-12 hrs. to give the corresp. benzyl alcohol (c) oxidation of the benzyl alcohol from stage (b) to give the corresp. aldehyde. Prods. have numerous uses e.g. benzaldehyde is used in the mfr. of dyes, flavours, etc., is an intermediate for mandelic and cinnamic acid prodn. and a solvent; benzyl alcohol is used as a bacteriostat and as a solvent for gelatine, casein and cellulose acetate; 3,4,5-trimethoxybenzaldehyde is an intermediate for trimethoprim. and other pharmaceuticals.
Priority Applications (20)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT4781178A IT1155794B (en) | 1978-01-27 | 1978-01-27 | Opt. substd. benzyl alcohol and benzaldehyde prepn. - by reacting benzoic acid with ethyl or isobutyl chloroformate to give benzoyl-ethyl-carbonate, then catalytic hydrogenation and opt. oxidn. |
NLAANVRAGE7900366,A NL186313C (en) | 1978-01-27 | 1979-01-17 | PROCESS FOR THE PREPARATION OF BENZYL ALCOHOLS AND BENZALDEHYDES |
CH47579A CH641752A5 (en) | 1978-01-27 | 1979-01-18 | PROCEDURE FOR THE PREPARATION OF AROMATIC ALCOHOLS. |
US06/004,447 US4239702A (en) | 1978-01-27 | 1979-01-18 | Process for preparing aromatic aldehydes and alcohols |
BE193029A BE873645A (en) | 1978-01-27 | 1979-01-23 | IMPROVED PROCESS FOR THE PREPARATION OF ALDEHYDES AND AROMATIC ALCOHOLS, IN PARTICULAR OF BENZALDEHYDE, BENZYL ALCOHOL AND THEIR DERIVATIVES |
DE19792902541 DE2902541A1 (en) | 1978-01-27 | 1979-01-24 | IMPROVED PROCESS FOR THE PRODUCTION OF AROMATIC ALDEHYDE AND ALCOHOLS, IN PARTICULAR BENZALDEHYDE, BENZYL ALCOHOL AND THEIR DERIVATIVES |
LU80835A LU80835A1 (en) | 1978-01-27 | 1979-01-26 | IMPROVED PROCESS FOR THE PREPARATION OF ALDEHYDES AND AQUE ALCOHOLS AND THEIR ROMATIC DERIVATIVES, IN PARTICULAR OF BENZALDEHYDE, BENZYLI ALCOHOL |
FR7902124A FR2415614A1 (en) | 1978-01-27 | 1979-01-26 | PROCESS FOR THE PREPARATION OF ALDEHYDES AND AROMATIC ALCOHOLS, IN PARTICULAR OF BENZALDEHYDE, BENZYL ALCOHOL AND THEIR DERIVATIVES |
DK33879A DK33879A (en) | 1978-01-27 | 1979-01-26 | PROCEDURE FOR THE PREPARATION OF AROMATIC ALDEHYDES OR ALCOHOLS |
AU43694/79A AU523640B2 (en) | 1978-01-27 | 1979-01-26 | Preparing aromatic aldehydes and alcohols |
PT7969138A PT69138A (en) | 1978-01-27 | 1979-01-26 | Improved process for preparing aromatic aldehydes and alcohols in particular benzaldehyde benzyl alcohol and derivatives thereof |
ES477207A ES477207A1 (en) | 1978-01-27 | 1979-01-26 | Process for preparing aromatic aldehydes and alcohols |
GB7902895A GB2013203B (en) | 1978-01-27 | 1979-01-26 | Process for preparing aromatic aldehydes and alcohols |
NO790258A NO149956C (en) | 1978-01-27 | 1979-01-26 | PROCEDURE FOR PREPARING BENZYL ALCOHOL AND DERIVATIVES THEREOF. |
AT0059779A AT364808B (en) | 1978-01-27 | 1979-01-26 | METHOD FOR PRODUCING BENZYL ALCOHOL AND SUBSTITUTED BENZYL ALCOHOLS |
SE7900715A SE448372B (en) | 1978-01-27 | 1979-01-26 | PROCEDURE FOR PREPARING BENZYL ALCOHOL AND DERIVATIVES THEREOF |
CA000320388A CA1121383A (en) | 1978-01-27 | 1979-01-26 | Process for preparing aromatic aldehydes and alcohols, in particular benzaldehyde, benzyl alcohol and derivatives thereof |
MX79101159U MX5736E (en) | 1978-01-27 | 1979-01-26 | PROCEDURE FOR PREPARING BENZYL ALCOHOL AND BENZALDEHYDE |
JP864779A JPS54112831A (en) | 1978-01-27 | 1979-01-27 | Manufacture of aromatic alcohol and aldehyde |
IE86/79A IE47646B1 (en) | 1978-01-27 | 1979-01-30 | Process for preparing aromatic aldehydes and alcohols |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT4781178A IT1155794B (en) | 1978-01-27 | 1978-01-27 | Opt. substd. benzyl alcohol and benzaldehyde prepn. - by reacting benzoic acid with ethyl or isobutyl chloroformate to give benzoyl-ethyl-carbonate, then catalytic hydrogenation and opt. oxidn. |
Publications (2)
Publication Number | Publication Date |
---|---|
IT7847811A0 IT7847811A0 (en) | 1978-01-27 |
IT1155794B true IT1155794B (en) | 1987-01-28 |
Family
ID=11262663
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IT4781178A IT1155794B (en) | 1978-01-27 | 1978-01-27 | Opt. substd. benzyl alcohol and benzaldehyde prepn. - by reacting benzoic acid with ethyl or isobutyl chloroformate to give benzoyl-ethyl-carbonate, then catalytic hydrogenation and opt. oxidn. |
Country Status (3)
Country | Link |
---|---|
AT (1) | AT364808B (en) |
BE (1) | BE873645A (en) |
IT (1) | IT1155794B (en) |
-
1978
- 1978-01-27 IT IT4781178A patent/IT1155794B/en active
-
1979
- 1979-01-23 BE BE193029A patent/BE873645A/en unknown
- 1979-01-26 AT AT0059779A patent/AT364808B/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
IT7847811A0 (en) | 1978-01-27 |
ATA59779A (en) | 1981-04-15 |
AT364808B (en) | 1981-11-25 |
BE873645A (en) | 1979-05-16 |
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