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

HRID 1066450Notes

Reaction equation

HRID 1066450 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>[OH:8][CH:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:10](=[CH2:11])[C:9]([O:13][CH3:14])=[O:12]

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 9237Dabco

Product 1

HCID 9942369Methyl 3-Hydroxy-2-methylene-3-phenylpropionateYield 94.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzaldehyde [formula (I), R1=Ph, 63.67 g (600 mmols)], 60 ml (667 mmols) of methyl acrylate [formula (II), R2=Me] and 13.46 g (120 mmols) of 1,4-diazabicyclo[2,2,2]octane were mixed, and stirred at room temperature for 119 hours. After the completion of the reaction, 60 ml of water, 60 ml of 37% hydrochloric acid and 120 ml of ethyl acetate were added to the reaction solution, and the organic layer was then extracted. The resulting organic layer was washed twice with 60 ml of a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, separated by filtration, and concentrated under reduced pressure to obtain 108.8 g of a crude product of the above title compound.

Workup

  1. additionwere added to the reaction solution
  2. extractionthe organic layer was then extracted
  3. washThe resulting organic layer was washed twice with 60 ml of a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customseparated by filtration
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-949f1cc626d6404e891ad5b2fd6d4fcd
Source dataset
uspto-grants-2001_06
Patent number
US06242635B1

Reaction notes

Loading…