Vinyl benzoate → 6-O-benzoylgalactal

HRID 1440002Notes

Reaction equation

HRID 1440002 reaction equation
[O:1]1[C@H:8]([CH2:9][OH:10])[C@H:6]([OH:7])[C@H:4]([OH:5])[CH:3]=[CH:2]1.[C:11](OC=C)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O>[C:11]([O:10][CH2:9][C@H:8]1[O:1][CH:2]=[CH:3][C@@H:4]([OH:5])[C@H:6]1[OH:7])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 13037Vinyl benzoateHCID 2734735D-Galactal

Product 1

HCID 143081066-O-benzoylgalactal

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.0 g (6.85 mmol) of galactal is taken up in 0.5-1.5 ml of H2O, 8 g of crushed molecular sieves are added, and the mixture is stirred with 1 g of Candida lipase AY-20 (Meito, Sangyo) or 1 g of lipase P (Amano) in 10-15 ml of vinyl benzoate at room temperature for 8-10 h. Filtering off the enzyme, concentration of the solution in vacuo, taking up the residue in ethyl acetate and extracting it with aqueous NaHCO3 solution, and subsequent chromatography on silica gel (ethyl acetate/hexane 1:1) result in 65-68% (about 1130 mg) of the desired 6-O-benzoylgalactal.

Workup

  1. addition8 g of crushed molecular sieves are added
  2. filtrationFiltering off the enzyme, concentration of the solution in vacuo
  3. extractionextracting it with aqueous NaHCO3 solution, and subsequent chromatography on silica gel (ethyl acetate/hexane 1:1)
  4. customresult in 65-68% (about 1130 mg) of the desired 6-O-benzoylgalactal

Sources & evidence

ORD record
ord-170d4d90beb7441ab5651619799246f9
Source dataset
uspto-grants-1996_03
Patent number
US05496930

Reaction notes

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