4-Hydroxybenzaldehyde → 1-(4-Hydroxyphenyl)-3-phenyl-1-propanol

HRID 1029445Notes

Reaction equation

HRID 1029445 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10]1([CH2:16][CH2:17][Mg]Br)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1.CCOCC>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[CH2:17][CH2:16][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 178419670HCID 178419670, compound

Product 1

HCID 197458831-(4-Hydroxyphenyl)-3-phenyl-1-propanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of p-hydroxybenzaldehyde (1.50 g) in THF (30 mL) was added dropwise a solution of 2-phenylethyl magnesium bromide in ether (15.2 mL, 1.7M) at 0°. After being stirred overnight at room temperature (RT) using a mechanical stirrer, it was poured onto a buffer (pH 7), extracted with ethyl acetate and the organic phase was dried and evaporated. The title compound was obtained after crystallization from ethyl acetate/hexane and was used directly in the next step.

Workup

  1. additionit was poured onto a buffer (pH 7)
  2. extractionextracted with ethyl acetate
  3. customthe organic phase was dried
  4. customevaporated

Sources & evidence

ORD record
ord-1e158be5af314190a4f8f619f51c2a9f
Source dataset
uspto-grants-1992_04
Patent number
US05102881

Reaction notes

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