2-Benzyloxy-4-(1,1-dimethylheptyl)benzaldehyde → trans-4-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-3-buten-2-one

HRID 1074481Notes

Reaction equation

HRID 1074481 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[C:15]([C:17]([CH3:25])([CH3:24])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:14]=[CH:13][C:10]=1[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClCCl>[CH2:1]([O:8][C:9]1[CH:16]=[C:15]([C:17]([CH3:25])([CH3:24])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:14]=[CH:13][C:10]=1/[CH:11]=[CH:10]/[C:9](=[O:8])[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 127882872-Benzyloxy-4-(1,1-dimethylheptyl)benzaldehyde

Product 1

HCID 12788289trans-4-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-3-buten-2-oneYield 147.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-benzyloxy-4-(1,1-dimethylheptyl)benzaldehyde (65.2 g, 0.193 mole) and of 1-triphenylphosphoranylidene-2-propane (62.0 g, 0.195 mole) in dichloromethane (195 ml) was heated at reflux for 20 hours. Another portion of 15.5 g ylid (15.5 g, 0.047 mole) was added and heating at reflux continued for 24 hours. The reaction mixture was cooled, evaporated and diluted with ether. The resulting precipitate of triphenylphosphine oxide was removed by filtration. The crude oil was purified via column chromatography on 1.5 kg of silica gel eluted with 20% etherhexane to yield 53.9 g (74%) of the title compound as an oil.

Workup

  1. temperatureat reflux for 20 hours
  2. additionAnother portion of 15.5 g ylid (15.5 g, 0.047 mole) was added
  3. temperatureheating
  4. temperatureat reflux
  5. temperatureThe reaction mixture was cooled
  6. customevaporated
  7. additiondiluted with ether
  8. customThe resulting precipitate of triphenylphosphine oxide was removed by filtration
  9. customThe crude oil was purified via column chromatography on 1.5 kg of silica gel
  10. washeluted with 20% etherhexane

Sources & evidence

ORD record
ord-0570deaff0a946dbbcecfa2386b7f710
Source dataset
uspto-grants-1983_07
Patent number
US04391827

Reaction notes

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