Hydrochloric Acid → Ethyl 3-hydroxy-3-(4'-cyclopentylphenyl)-butanoate

HRID 1582677Notes

Reaction equation

HRID 1582677 reaction equation
[CH:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.II.[CH2:17]([O:19][C:20](=[O:23])[CH2:21]Br)[CH3:18].Cl>C1C=CC=CC=1.[Zn]>[OH:14][C:12]([C:9]1[CH:8]=[CH:7][C:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:11][CH:10]=1)([CH3:13])[CH2:21][C:20]([O:19][CH2:17][CH3:18])=[O:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 7748Ethyl bromoacetateHCID 46579131-(4-Cyclopentylphenyl)ethanone

Product 1

HCID 11414712Ethyl 3-hydroxy-3-(4'-cyclopentylphenyl)-butanoateYield 88.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 241BenzeneSolvent

Procedure

To a refluxing mixture of 4′-cyclopentylacetophenone (17 g), I2 (5 mg) and Zn dust (12 g) in benzene (150 ml) was added ethylbromoacetate (11 ml) dropwise over 30 minutes. The mixture was refluxed for next 45 min and then cooled to room temperature. It was acidified with 10% aqueous HCl solution (150 ml) and organic layer was separated out. The organic layer was washed with water, dried (Na2SO4) and concentrated. The crude product was purified by column chromatography on silica gel to furnish 22 g (88.1% yield) of ethyl 3-hydroxy-3-(4′-cyclopentylphenyl)-butanoate (2a) as oil.

Workup

  1. temperatureThe mixture was refluxed for next 45 min
  2. customwas separated out
  3. washThe organic layer was washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e74bcc34dc73473797cd9abcfddfbeb0
Source dataset
uspto-grants-2004_05
Patent number
US06737438B2

Reaction notes

Loading…