Benzaldehyde → Methyl 3-Hydroxy-2-methylene-3-phenylpropionate

HRID 1081977Notes

Reaction equation

HRID 1081977 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N12CCN(CC1)CC2.[C:17]([O:21][CH3:22])(=[O:20])[CH:18]=[CH2:19].Cl>C(OCC)(=O)C>[OH:8][CH:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:18](=[CH2:19])[C:17]([O:21][CH3:22])=[O:20]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 9237Dabco

Product 1

HCID 9942369Methyl 3-Hydroxy-2-methylene-3-phenylpropionateYield 87.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

106 g (1 mol) of benzaldehyde (available from Nakarai Tesk K. K.), 11.2 g (0.1 mol) of 1,4-diazabicyclo[2,2,2]octane (available from Nacalai Tesque Inc.), and 90 ml (1 mol) of methyl acrylate (available from Nacalai Tesque Inc.) were stirred at room temperature over 7 days. To the reaction solution were then added 200 ml of a 6N hydrochloric acid and 200 ml of ethyl acetate so that an organic phase was extracted. The resulting organic phase was washed with a 10% brine, and then dried over magnesium sulfate. The solvent was then distilled off under reduced pressure. The residue was distilled under reduced pressure to obtain 167.8 g of the desired compound in the form of 99% purity colorless oily matter. When allowed to stand, the product was solidified. The product exhibited a melting point of from 34° to 36° C. (Yield: 87%)

Workup

  1. extractionwas extracted
  2. washThe resulting organic phase was washed with a 10% brine
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was then distilled off under reduced pressure
  5. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-4a676ed506594de2b12cea2cf4a6e09b
Source dataset
uspto-grants-1996_12
Patent number
US05587510

Reaction notes

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