3-Chloro-o-cresol → Benzyl Chloride

HRID 1416082Notes

Reaction equation

HRID 1416082 reaction equation
O[C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)C(O)=O.C(O[C:16]1[C:17]([CH3:25])=[C:18]([CH:22]=[CH:23][CH:24]=1)C(O)=O)(=O)C.[Cl:26][C:27]1[C:28]([CH3:34])=[C:29]([OH:33])[CH:30]=[CH:31][CH:32]=1>>[CH2:11]([Cl:26])[C:3]1[CH:4]=[CH:8][CH:9]=[CH:10][CH:2]=1.[CH2:25]([O:33][C:29]1[CH:30]=[CH:31][CH:32]=[C:27]([Cl:26])[C:28]=1[CH3:34])[C:17]1[CH:18]=[CH:22][CH:23]=[CH:24][CH:16]=1

Participants

5

Reactant 3

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

Product 2

HCID 7503Benzyl ChlorideHCID 117465342-Benzyloxy-6-chlorotoluene

Procedure

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) ##STR7## with benzyl chloride to give 2-benzyloxy-6-chlorotoluene (4) ##STR8## subjecting this to a Grignard reaction with magnesium to give (3-benzyloxy-2-methylphenyl)magnesium chloride (5) ##STR9## reacting this with CO2 to give 3-benzyloxy-2-methylbenzoic acid (6) ##STR10## 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-c469f498e33049929f868c34f344fb13
Source dataset
uspto-grants-1999_06
Patent number
US05910605

Reaction notes

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