Hydrochloric Acid → HCID 107657770, compound

HRID 629438Notes

Reaction equation

HRID 629438 reaction equation
F[C:2]1[C:10]([F:11])=[C:9]([CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[OH-].[Na+].CS(C)=[O:17].Cl>O.C(OCC)(=O)C>[F:11][C:10]1[C:2]([OH:17])=[C:3]([CH:7]=[CH:8][C:9]=1[CH3:12])[C:4]([OH:6])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 27741412,3-Difluoro-4-methylbenzoic acid

Product 1

HCID 107657770HCID 107657770, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2,3-difluoro-4-methylbenzoic acid (25.0 g), sodium hydroxide (23.2 g) and DMSO (250 mL) was stirred at 140° C. for 12 hr, and then overnight at room temperature, under argon atmosphere. To the reaction mixture was added 6M hydrochloric acid (100 mL) under ice-cooling. Ethyl acetate and water were added thereto at room temperature, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (24.3 g). This compound was used in the next step without an additional purification.

Workup

  1. customovernight
  2. customat room temperature
  3. temperaturecooling
  4. customat room temperature, the organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washwashed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6850f4b51435453d999b79af8b94edfb
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

Loading…