Acetic Acid → 3-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzoic Acid

HRID 2283166Notes

Reaction equation

[C:1]([OH:4])(=[O:3])[CH3:2].[CH:5]1([CH2:8][O:9][C:10]2[CH:11]=C([CH:15]=[CH:16][C:17]=2[O:18][CH:19]([F:21])[F:20])C=O)[CH2:7][CH2:6]1.S(=O)(=O)(O)N.Cl([O-])=O.[Na+]>O>[CH:5]1([CH2:8][O:9][C:10]2[CH:11]=[C:2]([CH:15]=[CH:16][C:17]=2[O:18][CH:19]([F:20])[F:21])[C:1]([OH:4])=[O:3])[CH2:6][CH2:7]1

Participants

Conditions

Temperature: 7.5 °C

Procedure

Glacial acetic acid (5 vol. with respect to 3-cyclopropylmethoxy 4-Difluoromethoxy benzaldehyde) was taken in a vessel and to this mixture of 3-cyclopropylmethoxy 4-Difluoromethoxy benzaldehyde and sulfamic acid (1.35 eq with respect to 3-cyclopropylmethoxy 4-Difluoromethoxy benzaldehyde) was added. The reaction mass was cooled to 5-10° C. under stirring. In another clean reaction vessel sodium chlorite (1.63 eq) was taken in water (1.5 vol. with respect to 3-cyclopropylmethoxy 4-Difluoromethoxy benzaldehyde) and added dropwise to the above prepared reaction solution at temperature below 10° C. The reaction mixture was stirred for 1 hr at 5-10° C. After completion of the reaction, water was added to get a white slurry. The solid was filtered and washed with water and dried under vacuum at 45-50° C. to get 3-cyclopropylmethoxy 4-Difluoromethoxy benzoic acid.

Workup

additionwas added
additionadded dropwise to the
customabove prepared
customreaction solution at temperature below 10° C
stirringThe reaction mixture was stirred for 1 hr at 5-10° C
additionwas added
customto get a white slurry
filtrationThe solid was filtered
washwashed with water
customdried under vacuum at 45-50° C.

Sources & evidence

ORD record: ord-127cd58cf7474c45a9b1ca3f67626e0e
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145365B2

Reaction notes

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