Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 3-(3-(benzyloxy)-4-methylphenyl)acrylate

HRID 709660Notes

Reaction equation

HRID 709660 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[CH3:17])[CH:12]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(=[CH:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:14]=[CH:15][C:16]=1[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 161013893-(Benzyloxy)-4-methylbenzaldehyde

Product 1

HCID 131733900Ethyl 3-(3-(benzyloxy)-4-methylphenyl)acrylateYield 76.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

Under a nitrogen atmosphere, to a solution of 3-(benzyloxy)-4-methylbenzaldehyde (2.50 g) in toluene (50 mL) was added ethyl (triphenylphosphoranylidene)acetate (4.20 g), and the mixture was stirred at 70° C. for 15 hr. The reaction mixture was concentrated, diethyl ether (100 mL) was added, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.50 g) as a colorless oil. This compound was used for the next step without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiethyl ether (100 mL) was added
  3. filtrationthe insoluble material was filtered off
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-50fd903ef6794fcc930d12baf51b1781
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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