3,5-Dimethoxybenzaldehyde → 1-(3,5-Dimethoxyphenyl)-8-bromo-1-octen-3-one

HRID 67883

Reaction equation

HRID 67883 reaction equation
[Br-:1].[O:2]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[CH:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH:36]=[C:37]([O:39][CH3:40])[CH:38]=1)[CH:34]=O>C1(C)C(C)=CC=CC=1>[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH:34]=[CH:9][C:3](=[O:2])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][Br:1])[CH:36]=[C:37]([O:39][CH3:40])[CH:38]=1

Participants

4

Reactant 2

HCID 817473,5-DimethoxybenzaldehydeHCID 71392763[(Oxepan-2-ylidene)methyl](triphenyl)phosphanium bromide

Product 1

HCID 544267451-(3,5-Dimethoxyphenyl)-8-bromo-1-octen-3-one

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

1.13 parts of [(2-oxepanylidene)methyl] triphenylphosphonium bromide having the formula ##STR11## was suspended and 0.83 part of 3,5-dimethoxybenzaldehyde was dissolved in 45 parts of xylene as the aprotic medium. This mixture was maintained under a nitrogen atmosphere and was refluxed for 24 hours and was then cooled to room temperature. Xylene was removed from the resulting clear solution at a temperature of about 60° C. and under reduced pressure. The remaining traces of xylene were removed in a drying oven at a temperature of about 50° C. and under a reduced pressure of about 0.5 millimeter of mercury. The resulting product mixture was separated chromatographically in a silica gel column using a benzene elution solvent, to isolate 1-(3,5-dimethoxyphenyl)-8-bromo-1-octen-3-one which, after recrystallization from benzene, melted at about 73°-76° C.

Workup

  1. temperatureThis mixture was maintained under a nitrogen atmosphere
  2. temperaturewas refluxed for 24 hours
  3. customXylene was removed from the resulting clear solution at a temperature of about 60° C. and under reduced pressure
  4. customThe remaining traces of xylene were removed in a drying oven at a temperature of about 50° C. and under a reduced pressure of about 0.5 millimeter of mercury
  5. customThe resulting product mixture was separated chromatographically in a silica gel column
  6. washa benzene elution solvent

Sources & evidence

ORD record
ord-e59a8289314448328373ff4fc93f237c
Source dataset
uspto-grants-1982_08
Patent number
US04347192

Linked notes

Loading…