Phenylacetaldehyde → HCID 10986812, compound

HRID 1506970Notes

Reaction equation

HRID 1506970 reaction equation
[C:1]1([CH2:7][CH:8]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(=[CH:29][C:30]([O:32][CH3:33])=[O:31])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:33][O:32][C:30](=[O:31])/[CH:29]=[CH:8]/[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 998PhenylacetaldehydeHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester

Product 1

HCID 10986812HCID 10986812, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of phenyl acetaldehyde (5.0 g, 41.61 mmol) in toluene (500 mL) was added methyl (triphenylphosphoranylidene)acetate (13.9 g, 41.61 mmol). The reaction mixture was stirred at reflux for 3 h. The resulting mixture was diluted with EtOAc, washed with water, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product was added ether/hexane (=1:1, v/v) at 0° C. then stirred for 30 min. The filtrate was concentrated then purified by a silica gel column to produce the title compound (5.9 g, 70˜90%)

Workup

  1. temperatureat reflux for 3 h
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. additionThe crude product was added ether/hexane (=1:1
  7. stirringv/v) at 0° C. then stirred for 30 min
  8. concentrationThe filtrate was concentrated
  9. customthen purified by a silica gel column

Sources & evidence

ORD record
ord-7153b6ac55d0424d806f4dd273ccb9cb
Source dataset
uspto-grants-2015_12
Patent number
US09221783B2

Reaction notes

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