p-Toluenesulfonic acid → Ethyl 3-(4-cyclopentylphenyl)but-2-enoate

HRID 1582678Notes

Reaction equation

HRID 1582678 reaction equation
O[C:2]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:12][CH:11]=1)([CH3:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.C([O-])(O)=O.[Na+]>[CH:16]1([C:13]2[CH:12]=[CH:11][C:10]([C:2]([CH3:9])=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:15][CH:14]=2)[CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 11414712Ethyl 3-hydroxy-3-(4'-cyclopentylphenyl)-butanoate

Product 1

HCID 69907173Ethyl 3-(4-cyclopentylphenyl)but-2-enoateYield 79.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of ethyl 3-hydroxy-(4′-cyclopentylphenyl)-butanoate (2a, 12 g) in benzene (150 ml) was added p-toluenesulfonic acid and refluxed for 1 h. The mixture was diluted with sat. NaHCO3 (100 ml) and organic layer was separated. The organic phase was washed with water, dried (Na2SO4) and concentrated. The crude product was purified by column chromatography on silica gel to give 8.9 g (79.4% yield) of ethyl 3-(4-cyclopentylphenyl)-but-2-enoate (3a, formula 3, R=cyclopentyl) as oil.

Workup

  1. temperaturerefluxed for 1 h
  2. customwas separated
  3. washThe organic phase 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-ae23d7cb453d469a82acb75a878d0ef9
Source dataset
uspto-grants-2004_05
Patent number
US06737438B2

Reaction notes

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