Benzyl Chloride → 2-Benzyloxy-6-chlorotoluene

HRID 1416072Notes

Reaction equation

HRID 1416072 reaction equation
O[C:2]1[C:3](C)=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.C(OC1C(C)=C(C=CC=1)C(O)=O)(=O)C.[Cl:26][C:27]1[C:28]([CH3:34])=[C:29](O)[CH:30]=[CH:31][CH:32]=1.C(Cl)C1C=CC=CC=1>>[CH2:5]([O:7][C:29]1[CH:30]=[CH:31][CH:32]=[C:27]([Cl:26])[C:28]=1[CH3:34])[C:4]1[CH:3]=[CH:2][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 4

HCID 7503Benzyl ChlorideHCID 148563-Chloro-o-cresolHCID 2520233-Hydroxy-2-methylbenzoic AcidHCID 37985573-Acetoxy-2-methylbenzoic acid

Product 1

HCID 117465342-Benzyloxy-6-chlorotoluene

Procedure

The invention relates to a process for the preparation of 3-hydroxy-2-methylbenzoic acid and 3-acetoxy-2-methylbenzoic acid, which comprises reacting 3-chloro-2-methylphenol (3) with benzyl chloride to give 2-benzyloxy-6-chlorotoluene (4) subjecting this to a Grignard reaction with magnesium to give (3-benzyloxy-2-methylphenyl)magnesium chloride (5) reacting this with CO2 to give 3-benzyloxy-2-methylbenzoic acid (6) hydrogenating this or its alkali metal salts in the presence of a hydrogenation catalyst to give 3-hydroxy-2-methylbenzoic acid (2) and optionally acetylating this to give 3-acetoxy-2-methylbenzoic acid.

Sources & evidence

ORD record
ord-e4b0fb45042c468087ac932fce50742e
Source dataset
uspto-grants-1999_06
Patent number
US05910605

Reaction notes

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