Hydrochloric Acid → 4-Phenylcyclohexane-1-carbaldehyde

HRID 1485055Notes

Reaction equation

HRID 1485055 reaction equation
C[O:2][CH:3]=[C:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.Cl.O.C(OCC)(=O)C>O1CCCC1>[C:10]1([CH:7]2[CH2:8][CH2:9][CH:4]([CH:3]=[O:2])[CH2:5][CH2:6]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 22167780HCID 22167780, compound

Product 1

HCID 155351504-Phenylcyclohexane-1-carbaldehydeYield 82.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution in tetrahydrofuran (10.0 mL) of the compound (3.59 g) obtained in step (1) above, 3 mol/L hydrochloric acid was added and the mixture was refluxed for 4 hours. After cooling the reaction mixture to room temperature, water was added to it and three extractions were conducted with ethyl acetate. The combined organic layers were washed with water and then concentrated under reduced pressure to give the titled compound as a colorless oil (2.75 g).

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. washThe combined organic layers were washed with water
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-38286e8de73d47358ac6c4445fc3cce7
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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