Methanol → Methyl 2-(3-methoxy-4-(trifluoromethyl)phenyl)acetate

HRID 1522897Notes

Reaction equation

HRID 1522897 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:13][C:14]([OH:16])=[O:15])[CH:6]=[CH:7][C:8]=1[C:9]([F:12])([F:11])[F:10].S(Cl)(Cl)=O.[CH3:21]O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:13][C:14]([O:16][CH3:21])=[O:15])[CH:6]=[CH:7][C:8]=1[C:9]([F:12])([F:11])[F:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 714638082-(3-Methoxy-4-(trifluoromethyl)phenyl)acetic acid

Product 1

HCID 86682916Methyl 2-(3-methoxy-4-(trifluoromethyl)phenyl)acetate

Procedure

To a solution of 2-(3-methoxy-4-(trifluoromethyl)phenyl)acetic acid (17.0 g, 72.6 mmol) in MeOH (200 mL), thionyl chloride (10 mL, 141 mmol) was added dropwise. The resulting mixture was stirred at room temperature for 16 h and concentrated under vacuum to afford the title compound (18.8 g). 1H NMR (DMSO-d6): δ 7.49 (s, 1H), 7.40 (d, 1H), 6.96 (d, 1H), 3.87 (s, 3H), 3.68 (s, 3H), 3.64-3.58 (m, 2H).

Workup

  1. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e5d3f57e8cd548ff953b069e1fc897e0
Source dataset
uspto-grants-2015_07
Patent number
US09078871B2

Reaction notes

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