Potassium Carbonate → 3-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzoic Acid

HRID 1776633Notes

Reaction equation

[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=2[O:14][CH:15]([F:17])[F:16])[CH:9]=[O:10])[CH2:3][CH2:2]1.[O-:18][Mn](=O)(=O)=O.[K+].C([O-])([O-])=O.[K+].[K+]>CC(C)=O.O>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=2[O:14][CH:15]([F:16])[F:17])[C:9]([OH:18])=[O:10])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzaldehyde (8.6 g, 35.5 mmol) in acetone (120 ml) and water (60 ml), KMnO4 (13.1 g, 70.8 mmol) was added and the reaction was heated at 60° C. for 1 h. K2CO3 (9 g, 65.2 mmol) and water (100 ml) were added, and the resulting mixture was filtered through a celite pad. The filtrate was acidified with HCl 37% (pH=1) and extracted twice with EtOAc. The organic phase was dried over Na2SO4 and the solvent was removed under vacuum affording 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoic acid (7.6 g, 29.4 mmol, 83% yield). This product was used without any further purification.

Workup

filtrationthe resulting mixture was filtered through a celite pad
extractionextracted twice with EtOAc
dry with materialThe organic phase was dried over Na2SO4
customthe solvent was removed under vacuum

Sources & evidence

ORD record: ord-2d37f57dda714ea5983b31a921824dcf
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09265768B2

Reaction notes

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