Hydrochloric Acid → HCID 22718782, compound

HRID 1582680Notes

Reaction equation

HRID 1582680 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.II.[CH2:18]([O:20][C:21](=[O:24])[CH2:22]Br)[CH3:19].Cl>C1C=CC=CC=1.[Zn]>[OH:15][C:13]([C:10]1[CH:9]=[CH:8][C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:12][CH:11]=1)([CH3:14])[CH2:22][C:21]([O:20][CH2:18][CH3:19])=[O:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 7748Ethyl bromoacetateHCID 877151-(4-Cyclohexylphenyl)ethan-1-one

Product 1

HCID 22718782HCID 22718782, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 241BenzeneSolvent

Procedure

To a refluxing mixture of 4′-cyclohexylacetophenone (25 g), I2 (5 mg) and Zn (17 g) in benzene (150 ml) was added ethylbromoacetate (20.7 ml) dropwise during 30 minutes. The mixture was refluxed for 2 h and then cooled to room temperature. It was acidified with 10% HCl (200 ml) an organic layer separated out. The organic phase was washed with water, dried (Na2SO4) and concentrated. The crude product was purified by column chromatography using SiO2 as adsorbent and hexane-ethylacetate mixture as eluant to give 28 g (80% yield) of ethyl 3-hydroxy-3-(4-cyclohexylphenyl)-butanoate (2b, formula 2, R=cyclohexyl) m.p. 45° C.

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. customseparated out
  3. washThe organic phase was washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-d4629483ed144d7f9c9e984c1317d449
Source dataset
uspto-grants-2004_05
Patent number
US06737438B2

Reaction notes

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