Hydrochloric Acid → (4-chlorophenyl)(2,2-difluorocyclopentyl)acetic Acid

HRID 1476082Notes

Reaction equation

HRID 1476082 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:14]2[CH2:18][CH2:17][CH2:16][C:15]2([F:20])[F:19])[C:9]([O:11]CC)=[O:10])=[CH:4][CH:3]=1.C1COCC1.[OH-].[Na+].Cl>CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH:14]2[CH2:18][CH2:17][CH2:16][C:15]2([F:19])[F:20])[C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58288188Ethyl(4-chlorophenyl)(2,2-difluorocyclopentyl)acetate

Product 1

HCID 58288424(4-chlorophenyl)(2,2-difluorocyclopentyl)acetic Acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

2.70 g (8.92 mmol) of ethyl (4-chlorophenyl)(2,2-difluorocyclopentyl)acetate (diastereomer mixture) were dissolved in 10 ml of methanol, 10 ml of THF and 5 ml of water, and 7.13 g (89.18 mmol) of 50% strength aqueous sodium hydroxide solution were added at RT. The reaction mixture was stirred at RT overnight. The mixture was then diluted with water and acidified with hydrochloric acid. The aqueous phase was extracted three times with ethyl acetate, the combined organic phases were dried over magnesium sulphate and concentrated under reduced pressure and the residue was dried under high vacuum. This gave 2.39 g of the title compound (97.6% of theory, diastereomer ratio about 1:1).

Workup

  1. extractionThe aqueous phase was extracted three times with ethyl acetate
  2. dry with materialthe combined organic phases were dried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-c208c7e9c9164ce18981829428ff7112
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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