Chlorodifluoromethane → 3-Chloro-5-(difluoromethoxy)benzoic acid

HRID 1246643Notes

Reaction equation

HRID 1246643 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5]([OH:7])=[O:6].[OH-].[Na+].Cl[CH:15]([F:17])[F:16]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH:15]([F:17])[F:16])[CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 6372ChlorodifluoromethaneHCID 14798Sodium HydroxideHCID 130716463-Chloro-5-hydroxybenzoic Acid

Product 1

HCID 219046063-Chloro-5-(difluoromethoxy)benzoic acidYield 75.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Chloro-5-hydroxybenzoic acid (6.4 g, 37.2 mmol; see step (ii) above) dissolved in chloroform (200 mL) was transferred to a 500 mL three-necked round-bottomed flask fitted with a dry ice condenser and a gas inlet tube. Sodium hydroxide (100 mL, 5 M) was added and with vigorous stirring. Chlorodifluoromethane (Freon 22; 25 g, 290 mmol) was added portionwise through the gas inlet tube at ambient temperature. After 2 hours, the reaction was complete. Extractive work up gave 6.2 g, 28 mmol (yield: 75%) of the sub-title compound.

Workup

  1. customwas transferred to a 500 mL three-necked round-bottomed flask
  2. customfitted with a dry ice condenser and a gas inlet tube

Sources & evidence

ORD record
ord-feb156be9d4e498f92db71c4b095b225
Source dataset
uspto-grants-2006_10
Patent number
US07129233B2

Reaction notes

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