p-Toluenesulfonic acid → Ethyl 3-(4'-chloro-[1,1'-biphenyl]-4-yl)-but-2-enoate

HRID 1582693Notes

Reaction equation

HRID 1582693 reaction equation
O[C:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH: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.C([O-])(O)=O.[Na+]>C1C=CC=CC=1.O>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([C:13]2[CH:14]=[CH:15][C:10]([C:2]([CH3:9])=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:11][CH:12]=2)=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 22718790Ethyl 3-hydroxy-3-(4'-chloro-[1,1'-biphenyl]-4-yl)-butanoate

Product 1

HCID 69798367Ethyl 3-(4'-chloro-[1,1'-biphenyl]-4-yl)-but-2-enoateYield 91%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a solution of crude ethyl 3-hydroxy-3-(4′-chloro-[1,1′-biphenyl]-4-yl)-butanoate (2g) in benzene (200 ml) was added p-toluenesulfonic acid (3 gm) and was refluxed for 3 h 30 minutes. The reaction mixture was cooled, neutralized with NaHCO3 solution, diluted with water and organic layer was extracted. Organic layer was washed with water, dried (NaHCO3) and concentrated. Crude product was purified by column chromatography on silica gel to furnish 5.27 g (47.=91% yield) of ethyl 3-(4′-chloro-[1,1′-biphenyl]-4-yl)-but-2-enoate (3g, formula 3, R=p-Cl—C6H4) m.p. 91-94° C.

Workup

  1. temperaturewas refluxed for 3 h 30 minutes
  2. temperatureThe reaction mixture was cooled
  3. extractionwas extracted
  4. washOrganic layer was washed with water
  5. dry with materialdried (NaHCO3)
  6. concentrationconcentrated
  7. customCrude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-04f5395ea3eb4c8d9992a788c5a84720
Source dataset
uspto-grants-2004_05
Patent number
US06737438B2

Reaction notes

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