(Triphenylphosphoranylidene)acetaldehyde → (2E)-2-Octadecenal

HRID 1710174Notes

Reaction equation

HRID 1710174 reaction equation
[CH:1](=[O:17])[CH:2]=[CH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH:18]([CH:20]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O>C1(C)C=CC=CC=1>[CH:1](=[O:17])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:18][CH3:20]

Participants

4

Reactant 2

HCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 1456842-Hexadecenal

Product 1

HCID 5463317(2E)-2-Octadecenal

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

12 g (50 mmol) of hexadecenal and 15.2 g (50 mmol) of formylmethylenetriphenylphosphorane in 250 ml of anhydrous toluene are boiled under reflux for 8 hours. The mixture is evaporated to dryness. The residue is extracted five times with 100 ml of ether. The extract is evaporated to dryness and chromatographed on silica gel using toluene. Yield: 8.2 g (62%). Melting point: 35° C.; RF =0.8, toluene/ethyl acetate 8:2.

Workup

  1. temperatureunder reflux for 8 hours
  2. customThe mixture is evaporated to dryness
  3. extractionThe residue is extracted five times with 100 ml of ether
  4. customThe extract is evaporated to dryness
  5. customchromatographed on silica gel

Sources & evidence

ORD record
ord-6da7c0e574aa4e3ca4a2a086e3007191
Source dataset
uspto-grants-1990_08
Patent number
US04952683

Reaction notes

Loading…