HCID 54210642, compound → (1-Cyanocyclohexyl)acetic acid

HRID 1862581Notes

Reaction equation

HRID 1862581 reaction equation
C([O:8][C:9](=[O:19])[CH2:10][C:11]1([C:17]#[N:18])[CH:16]=[CH:15][CH2:14][CH:13]=[CH:12]1)C1C=CC=CC=1>[Pd].[O-]S([O-])(=O)=O.[Ba+2].CO>[C:17]([C:11]1([CH2:10][C:9]([OH:19])=[O:8])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)#[N:18]

Participants

4

Reactant 1

HCID 54210642HCID 54210642, compound

Product 1

HCID 11073797(1-Cyanocyclohexyl)acetic acidYield 87%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalyst2×HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Added 5% Pd/BaSO4 catalyst (9.0 mg, 4.2 μmol) to a solution of (1-cyanocyclohexa-2,5-dienyl)acetic acid benzyl ester (1.00 g, 3.95 mmol) in MeOH (20 mL). After stirring the reaction mixture under an atmosphere of H2 at 0° C. for 0.5 hour and room temperature for 1.5 hours, additional 5% Pd/BaSO4 (75.8 mg, 35.6 μmol) was added. After stirring the reaction mixture under an atmosphere of H2 at 0° C. for 1 hour and room temperature for 19.5 hours, the reaction was filtered and concentrated under reduced pressure to afford 0.56 g (87%) of crude oil.

Workup

  1. waitroom temperature for 1.5 hours
  2. stirringAfter stirring the reaction mixture under an atmosphere of H2 at 0° C. for 1 hour
  3. waitroom temperature for 19.5 hours
  4. filtrationthe reaction was filtered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3dcd81d6f664447d9339db29479fec5e
Source dataset
uspto-grants-2003_03
Patent number
US06538148B2

Reaction notes

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