Toluene → (E)-ethyl 3-(5-hydroxy-[1,1'-biphenyl]-2-yl)acrylate

HRID 2069636

Reaction equation

HRID 2069636 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]([CH:14]=O)=[CH:4][CH:3]=1.[C:16]([CH:19]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:18])=[O:17].[C:39]1(C)C=CC=C[CH:40]=1>>[OH:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:14]=[CH:19]/[C:16]([O:18][CH2:39][CH3:40])=[O:17])=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 10870911Carboxymethylene triphenylphosphoraneHCID 573034645-Hydroxy-[1,1'-biphenyl]-2-carbaldehyde

Product 1

HCID 58566652(E)-ethyl 3-(5-hydroxy-[1,1'-biphenyl]-2-yl)acrylate

Procedure

A solution of 5-hydroxy-[1,1′-biphenyl]-2-carbaldehyde (651) (292 mg, 1.47 mmol) and (carboxymethylene)-triphenylphosphorane (564.5 mg, 1.62 mmol) in toluene (15 mL) was refluxed for 24 hours. The reaction was concentrated in vacuo and was purified by flash column chromatography on silica gel with hexanes and EtOAc (30%) to give (E)-ethyl 3-(5-hydroxy-[1,1′-biphenyl]-2-yl)acrylate (652).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customwas purified by flash column chromatography on silica gel with hexanes and EtOAc (30%)

Sources & evidence

ORD record
ord-73a19d5aa75645cda34aa78636ac221c
Source dataset
uspto-grants-2012_10
Patent number
US08299117B2

Linked notes

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