GB1360137A - Preparation of saligenol - Google Patents
Preparation of saligenolInfo
- Publication number
- GB1360137A GB1360137A GB1697772A GB1697772A GB1360137A GB 1360137 A GB1360137 A GB 1360137A GB 1697772 A GB1697772 A GB 1697772A GB 1697772 A GB1697772 A GB 1697772A GB 1360137 A GB1360137 A GB 1360137A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- glycol
- saligenol
- borates
- treating
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 title abstract 11
- 238000002360 preparation method Methods 0.000 title abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 6
- -1 alkylene borates Chemical class 0.000 abstract 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 150000001642 boronic acid derivatives Chemical class 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 2
- 239000011707 mineral Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- QPYKYDBKQYZEKG-UHFFFAOYSA-N 2,2-dimethylpropane-1,1-diol Chemical compound CC(C)(C)C(O)O QPYKYDBKQYZEKG-UHFFFAOYSA-N 0.000 abstract 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 229930195725 Mannitol Natural products 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 abstract 1
- 239000004327 boric acid Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000013522 chelant Substances 0.000 abstract 1
- 238000000354 decomposition reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- AVIYEYCFMVPYST-UHFFFAOYSA-N hexane-1,3-diol Chemical compound CCCC(O)CCO AVIYEYCFMVPYST-UHFFFAOYSA-N 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000000594 mannitol Substances 0.000 abstract 1
- 235000010355 mannitol Nutrition 0.000 abstract 1
- 229920000151 polyglycol Polymers 0.000 abstract 1
- 239000010695 polyglycol Substances 0.000 abstract 1
- 239000000600 sorbitol Substances 0.000 abstract 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/11—Alkylated hydroxy benzenes containing also acyclically bound hydroxy groups, e.g. saligenol
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1360137 Saligenol; alkylene borates SUMITOMO CHEMICAL CO Ltd 12 April 1972 [12 April 1971] 16977/72 Headings C2B and C2C Saligenol (o-hydroxymethyl phenol) is prepared by "decomposing" a borate of formula in which R is group containing 2-10 carbon atoms which is the residue of a glycol or polyglycol of formula HO-R-OH. The decomposition referred to above may be carried out by (a) forming an alkali metal salt by treating with an alkali metal hydroxide and treating this with a mineral acid or with a compound which forms stronger chelate linkages with boric' acid than with saligenol, e.g. mannitol, or sorbitol; (b) treating it with a C 1 -C 6 alcohol to form a volatile boric ester which is distilled off; or (c) hydrolysing it with a dilute mineral and extracting the saligenol with a suitable solvent. R may be, for example, derived from ethylene glycol, and sinethylene glycol, 2,2- dimethylpropane diol, 1,3-hexylene glycol, diethylene glycol or triethylene glycol. Phenyl alkylene borates or phenylpolyalkylene borates of formula in which R is as defined above and may be prepared by reacting equimolar amount of phenol, boric acid and a glycol of formula HO-R-OH in a solvent under azeotropic dehydrating conditions; the products may be converted to compounds of Formula II above by treatment with formaldehyde or a substance yielding formaldehyde. Examples describe the preparation of borates of the latter formula in which R is -CH 2 -CH 2 -, and
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2325171A JPS5129143B1 (en) | 1971-04-12 | 1971-04-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1360137A true GB1360137A (en) | 1974-07-17 |
Family
ID=12105365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1697772A Expired GB1360137A (en) | 1971-04-12 | 1972-04-12 | Preparation of saligenol |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5129143B1 (en) |
| BE (1) | BE781983A (en) |
| CA (1) | CA967172A (en) |
| CH (1) | CH579520A5 (en) |
| DE (1) | DE2217626C3 (en) |
| FR (1) | FR2132861B1 (en) |
| GB (1) | GB1360137A (en) |
| IT (1) | IT954654B (en) |
| NL (1) | NL7204820A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51125035A (en) * | 1974-10-09 | 1976-11-01 | Shionogi & Co Ltd | New process for preparing 0-hydroxybenzylalcohols |
| FR2430928A1 (en) * | 1978-07-11 | 1980-02-08 | Rhone Poulenc Ind | PROCESS FOR THE PREPARATION OF ORTHOHYDROXYBENZYL ALCOHOLS |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1074952A (en) * | 1952-02-21 | 1954-10-11 | Shell Refining & Marketing Co | Liquid fuels for internal combustion engines and their additives |
| US3523014A (en) * | 1967-11-13 | 1970-08-04 | Standard Oil Co | Borated monoalkyl dihydroxybenzenes |
-
1971
- 1971-04-12 JP JP2325171A patent/JPS5129143B1/ja active Pending
-
1972
- 1972-03-30 CA CA138,588A patent/CA967172A/en not_active Expired
- 1972-04-11 NL NL7204820A patent/NL7204820A/xx unknown
- 1972-04-11 IT IT6812072A patent/IT954654B/en active
- 1972-04-11 FR FR7212666A patent/FR2132861B1/fr not_active Expired
- 1972-04-12 DE DE19722217626 patent/DE2217626C3/en not_active Expired
- 1972-04-12 GB GB1697772A patent/GB1360137A/en not_active Expired
- 1972-04-12 CH CH536372A patent/CH579520A5/xx not_active IP Right Cessation
- 1972-04-12 BE BE781983A patent/BE781983A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE781983A (en) | 1972-07-31 |
| FR2132861B1 (en) | 1976-08-06 |
| CH579520A5 (en) | 1976-09-15 |
| FR2132861A1 (en) | 1972-11-24 |
| DE2217626A1 (en) | 1972-10-19 |
| DE2217626B2 (en) | 1973-12-06 |
| JPS5129143B1 (en) | 1976-08-24 |
| IT954654B (en) | 1973-09-15 |
| DE2217626C3 (en) | 1974-07-25 |
| NL7204820A (en) | 1972-10-16 |
| CA967172A (en) | 1975-05-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |