Methyl Acrylate → 2-Propenoic acid, 4-(2-oxiranylmethoxy)butyl ester

HRID 1926562Notes

Reaction equation

HRID 1926562 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10])[CH:2]1[O:4][CH2:3]1.[C:11](OC)(=[O:14])[CH:12]=[CH2:13]>>[CH2:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][CH2:7][CH2:6][O:5][CH2:1][CH:2]1[O:4][CH2:3]1)=[O:14]

Participants

3

Reactant 2

HCID 7294Methyl AcrylateHCID 197857804-[(Oxiran-2-yl)methoxy]butan-1-ol

Product 1

HCID 98155892-Propenoic acid, 4-(2-oxiranylmethoxy)butyl ester

Conditions

Temperature
40 °C

Procedure

In each case 20 mMol of 4-hydroxybutyl glycidyl ether (2.92 g) were stirred with 80 mMol of methyl acrylate (6.89 g), 100 mg of Novozym® 435 and 4.0 g of 5 Å molecular sieve were stirred at 20 or 40° C. for 2, 4, 6, 8 or 24 h. Thereafter, the enzyme was filtered off and the excess of methyl acrylate was removed on a rotary evaporator. A colorless acrylate was obtained with 93% (at 20° C.) or 94% (at 40° C.) yield.

Workup

  1. filtrationThereafter, the enzyme was filtered off
  2. customthe excess of methyl acrylate was removed on a rotary evaporator

Sources & evidence

ORD record
ord-edfaff76660f4b42821b59a89ad3780d
Source dataset
uspto-grants-2012_05
Patent number
US08183018B2

Reaction notes

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