Hydrochloric Acid → alpha-Cyclopentyl-p-hydroxybutyrophenone

HRID 637376Notes

Reaction equation

HRID 637376 reaction equation
[CH:1]1([CH:6]([CH2:17][CH3:18])[C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][CH:10]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl-].[Cl-].[Cl-].[Al+3].Cl>C1C=CC=CC=1>[CH:1]1([CH:6]([CH2:17][CH3:18])[C:7]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 13175264alpha-Cyclopentyl-p-methoxybutyrophenone

Product 1

HCID 13175265alpha-Cyclopentyl-p-hydroxybutyrophenone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The mixture of 4.9 g (0.02 mol) of α-cyclopentyl-p-methoxy butyrophenone, 8.0 g (0.06 mol) of aluminium trichloride and 60 ml of benzene was refluxed for 3 hours. Dilute hydrochloric acid was added, the layers separated and the organic layer washed with water. The product was extracted with 2M sodium hydroxide. The alkaline solution was made acidic. The product was extracted with methylene chloride, dried and the solvent evaporated. The residue 4.1 g (0.018 mol, 88%) was crystallized from petroleum ether. Mp. 75°-78° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. customthe layers separated
  3. washthe organic layer washed with water
  4. extractionThe product was extracted with 2M sodium hydroxide
  5. extractionThe product was extracted with methylene chloride
  6. customdried
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-8dadc59f99e94a73b861f46460cb8c9b
Source dataset
uspto-grants-1985_12
Patent number
US04556677

Reaction notes

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