4-Chloro-2-methylbenzoic acid → 4-Chloro-2-methylbenzyl Alcohol

HRID 1690840Notes

Reaction equation

HRID 1690840 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([CH3:11])[CH:3]=1.C(O)C.C(OCC)(OCC)OCC.S(=O)(=O)(O)O>O1CCCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[C:4]([CH3:11])[CH:3]=1

Participants

4

Reactant 2

HCID 3482694-Chloro-2-methylbenzoic acidHCID 86638451Ethanol triethyl orthoformate sulfuric acid

Product 1

HCID 27576694-Chloro-2-methylbenzyl AlcoholYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A sample of 4-chloro-2-methylbenzoic acid was converted to the ethyl ester using ethanol/triethyl orthoformate/sulfuric acid in >95% yield. Reduction of the ester with LiAiH4/tetrahydrofuran gave 4-chloro-2-methylbenzyl alcohol in 97% yield as a colorless oil. Subsequent treatment with thionyl chloride/pyridine/CH2Cl2 gave the substituted benzyl chloride. The latter, on treatment with 40% excess sodium cyanide in DMF at 90° C. for 20 min. and normal work-up and crystallization from hexane/butyl chloride (2 crops) gave 4-chloro-2-methylbenzyl cyanide in 80% overall yield.

Sources & evidence

ORD record
ord-fa5e78304bd74a8cbc51bae2fd7db01a
Source dataset
uspto-grants-2012_04
Patent number
US08153688B2

Reaction notes

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