Diethyl Ether → HCID 54456843, compound

HRID 1018470Notes

Reaction equation

HRID 1018470 reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)[CH3:2].[CH:12]([C:14](=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:15])=[O:13].C(OCC)C>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[C:14]([CH3:15])[CH:12]=[O:13])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 248344-EthoxybenzaldehydeHCID 42809872-(Triphenylphosphoranylidene)propionaldehyde

Product 1

HCID 54456843HCID 54456843, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 4-ethoxybenzaldehyde (20 g, 0.133 mol) and α-formylethylidenetriphenylphosphorane (46.6 g, 0.146 mol) in dried toluene (400 ml) was heated with stirring at reflux under an atmosphere of nitrogen for 40 h. The mixture was cooled, diethyl ether added and filtered through a pad of celite. The filtrate was evaporated and the residue taken up in diethyl e;her and the resulting suspension purified on flash silica eluting with hexane-diethyl ether (4:1). The resulting oil was crystallised from hexane-diethyl ether to give 3-(4-ethoxyphenyl)-2-methylpropenaldehyde as yellow crystals.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under an atmosphere of nitrogen for 40 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered through a pad of celite
  5. customThe filtrate was evaporated
  6. customthe resulting suspension purified on flash silica eluting with hexane-diethyl ether (4:1)
  7. customThe resulting oil was crystallised from hexane-diethyl ether

Sources & evidence

ORD record
ord-0754702ebba14b2d9053bb092bd3bad4
Source dataset
uspto-grants-2002_11
Patent number
US06482824B1

Reaction notes

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