Acetic Acid → 4-(Difluoromethoxy)-3-methoxybenzoic acid

HRID 727380Notes

Reaction equation

HRID 727380 reaction equation
Cl([O-])=O.[Na+].[F:5][CH:6]([F:18])[O:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][C:9]=1[O:16][CH3:17].S(=O)(=O)([OH:21])N.C(O)(=O)C>O>[F:5][CH:6]([F:18])[O:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]([OH:21])=[O:13])=[CH:10][C:9]=1[O:16][CH3:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5987Sulfamic AcidHCID 31612494-(Difluoromethoxy)-3-methoxybenzaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 20604514-(Difluoromethoxy)-3-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 7.3 g of 80% strength sodium chlorite in 15 ml of water is added dropwise with continuous stirring to a mixture of 10.0 g of 4-difluoromethoxy-3-methoxybenzaldehyde, 6.5 g of sulphamic acid and 50 ml of glacial acetic acid. The internal temperature is kept between 30° and 35° C. by cooling with ice water. After dropwise addition is complete, the mixture is stirred for a further 1 h and then diluted with water. The precipitated 4-difluoromethoxy-3-methoxybenzoic acid is filtered off with suction, washed with water, dried in vacuo and crystallized from acetonitrile/petroleum ether (b.p. 40°) 2/8. Yield 7.1 g; m.p. 170° C.

Workup

  1. customis kept between 30° and 35° C.
  2. additionAfter dropwise addition
  3. filtrationThe precipitated 4-difluoromethoxy-3-methoxybenzoic acid is filtered off with suction
  4. washwashed with water
  5. customdried in vacuo
  6. customcrystallized from acetonitrile/petroleum ether (b.p. 40°) 2/8

Sources & evidence

ORD record
ord-42e802cb84274926881f0c241cce64b6
Source dataset
uspto-grants-1998_01
Patent number
US05712298

Reaction notes

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