HCID 40793572, compound → Hexahydrophthalic anhydride, cis-

HRID 2188333Notes

Reaction equation

HRID 2188333 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]([C@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[C:17]([OH:19])=[O:18])=[O:10])[CH:5]=[C:6]([F:8])[CH:7]=1>[OH-].[Na+]>[F:1][C:2]1[CH:3]=[C:4]([C:9]([C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]2[C:17]([OH:19])=[O:18])=[O:10])[CH:5]=[C:6]([F:8])[CH:7]=1.[C@@H:11]12[C:9](=[O:10])[O:19][C:17](=[O:18])[C@@H:12]1[CH2:13][CH2:14][CH2:15][CH2:16]2

Participants

4

Reactant 1

HCID 40793572HCID 40793572, compound

Product 2

HCID 641660Hexahydrophthalic anhydride, cis-HCID 40793565HCID 40793565, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
20 °C

Procedure

Cis-2-(3,5-difluorophenylcarbonyl)cyclohexanecarboxylic acid was dissolved in 10% NaOH (250 mL) and the solution was stirred at 20° C. for 16 h. The aqueous solution was extracted with diethyl ether (100 mL), and then acidified with 1M hydrochloric acid. The resulting precipitate was collected, and recrystallized from CH2Cl2/hexanes, to give (1S, 2R)-2-(3,5-difluorophenyl-carbonyl)cyclohexanecarboxylic acid as a white solid (4 g, 30% from cis-1,2-cyclohexanedicarboxylic anhydride).

Workup

  1. extractionThe aqueous solution was extracted with diethyl ether (100 mL)
  2. customThe resulting precipitate was collected
  3. customrecrystallized from CH2Cl2/hexanes

Sources & evidence

ORD record
ord-3b68d02da2ff43b6a87a9ba4e45536ce
Source dataset
uspto-grants-2002_06
Patent number
US06410781B1

Reaction notes

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