p-Toluenesulfonic acid → HCID 69906260, compound

HRID 1582685Notes

Reaction equation

HRID 1582685 reaction equation
O[C:2]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:23][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+].O>[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][CH2:23]1

Participants

6

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 22718798HCID 22718798, compound

Product 1

HCID 69906260HCID 69906260, compoundYield 81.1%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent2×HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of ethyl 3-hydroxy-3-(4′-cyclooctylphenyl)-butanoate (2d, 36 g) in benzene (350 ml) was added p-toluenesulfonic acid and refluxed for 2.5 h. The mixture was diluted with saturated NaHCO3 solution (20 ml) and water (50 ml) and benzene layer was separated out. Aqueous layer was extracted with benzene (2×200 ml) combined organic layer was washed with water (2×20 ml), dried over Na2SO4 and concentrated. Crude product was purified by column chromatography to furnish 27.5 g (81.1% yield) of ethyl 3-(4′-cyclooctylphenyl)-but-2-enoate (3d, formula 3, R=cyclooctyl) as oil.

Workup

  1. temperaturerefluxed for 2.5 h
  2. customwas separated out
  3. extractionAqueous layer was extracted with benzene (2×200 ml)
  4. washwas washed with water (2×20 ml)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customCrude product was purified by column chromatography

Sources & evidence

ORD record
ord-35e34cf78c3e441e88adaf09bedab520
Source dataset
uspto-grants-2004_05
Patent number
US06737438B2

Reaction notes

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