Methanol → Methyl 2-fluoro-4-methylbenzoate

Reaction equation

[F:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12]O>>[CH3:12][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:2]=1[F:1]

Participants

Reactant 2

HCID 887Methanol

HCID 27361452-Fluoro-4-methylbenzoic acid

Product 1

HCID 18759805Methyl 2-fluoro-4-methylbenzoate

Procedure

2-Fluoro-4-methylbenzoic acid (30.0 g, 195 mmol) was dissolved in MeOH (600 mL, 10 mol), and 12 M HCl (3.2 mL, 39 mmol) was added. The mixture was heated to reflux and stirred for 48 hours, then cooled and concentrated. The recovered material was dried in vacuo for 24 hours to obtain Intermediate (6a) as a white solid that was used without further purification.

Workup

temperatureThe mixture was heated
temperatureto reflux
temperaturecooled
concentrationconcentrated
customThe recovered material was dried in vacuo for 24 hours

Sources & evidence

ORD record: ord-de11b31c9e924d26bc575932cd588fc0
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637676B2

Reaction notes

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