Hydrochloric Acid → Ethyl 3-hydroxy-3-([1,1'-biphenyl]-4yl)butanoate

HRID 1582687Notes

Reaction equation

HRID 1582687 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].II.[CH2:18]([O:20][C:21](=[O:24])[CH2:22]Br)[CH3:19].Cl>C1C=CC=CC=1.[Zn]>[OH:3][C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([CH3:2])[CH2:22][C:21]([O:20][CH2:18][CH3:19])=[O:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 71134-AcetylbiphenylHCID 7748Ethyl bromoacetate

Product 1

HCID 12455957Ethyl 3-hydroxy-3-([1,1'-biphenyl]-4yl)butanoateYield 72.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 241BenzeneSolvent2×

Procedure

To a refluxing mixture of 4-acetylbiphenyl (20 g), I2 (5 mg) and Zn (6.8 g) in benzene (200 ml) was added ethylbromoacetate (12 ml) dropwise during 30 minutes. The mixture was refluxed for 1 h and then cooled to room temperature. It was acidified with 10% HCl (100 ml) 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 20.6 g (72.1% yield) of ethyl 3-hydroxy-3-([1,1′-biphenyl]-4yl)butanoate (2e, formula 2, R=Ph) m.p. 58-60° C.

Workup

  1. temperatureThe mixture was 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-120553561abd4e709ef8b6109a55b72e
Source dataset
uspto-grants-2004_05
Patent number
US06737438B2

Reaction notes

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