p-Toluenesulfonic acid → HCID 69907470, compound

HRID 1582683Notes

Reaction equation

HRID 1582683 reaction equation
O[C:2]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:22][CH2:21][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][CH2:21][CH2:22]1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 22718777HCID 22718777, compound

Product 1

HCID 69907470HCID 69907470, compoundYield 42.9%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of ethyl 3-hydroxy-3-(4′-cycloheptylphenyl)-butanoate (2c, 28.75 g) in benzene (175 ml) was added p-toluenesulfonic acid and was refluxed for 1 h. The reaction mixture was diluted with NaHCO3 and benzene 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 give 11.6 g (42.9% yield) of ethyl 3-(4′-cycloheptylphenyl)-but-2-enoate (3c, formula 3, R=cycloheptyl) as viscous oil.

Workup

  1. temperaturewas refluxed for 1 h
  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-19269e2e21b14ed28fbf30e5aa705ec9
Source dataset
uspto-grants-2004_05
Patent number
US06737438B2

Reaction notes

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