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

HRID 1979097Notes

Reaction equation

HRID 1979097 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:13][CH3:14])(=[O:12])[CH:10]=[CH2:11].N12CCN(CC1)CC2.Cl>C(OCC)(=O)C.O>[CH3:14][O:13][C:9](=[O:12])[C:10](=[CH2:11])[CH:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 9237Dabco

Product 1

HCID 9942369Methyl 3-Hydroxy-2-methylene-3-phenylpropionate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of benzaldehyde (63.67 g; 600 mmol), methyl acrylate (60 ml; 667 mmol) and 1,4-diazabicyclo [2.2.2] octane (13.46 g; 120 mmol) is stirred at ambient temperature for 119 hours. To the reaction solution is added water (60 ml), 37% hydrochloric acid (60 ml) and ethyl acetate (120 ml), and then, the organic phase is extracted. The resulting organic phase is washed twice with saturated saline (60 ml), dried over anhydrous sodium sulfate and filtered, then concentrated under reduced pressure, to give a crude product of the title compound at a yield of 108.8 g. 1H-NMR (CDCl3) d: 3.12 (1H, s), 3.69 (3H, s), 5.55 (1H, s), 5.83 (1H, s), 6.33 (1H, s), 7.29-7.37 (5H, m).

Workup

  1. extractionthe organic phase is extracted
  2. washThe resulting organic phase is washed twice with saturated saline (60 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1af3c47aa9bb4b98b1b1c1c8871637a9
Source dataset
uspto-grants-2001_05
Patent number
US06239305B1

Reaction notes

Loading…