Acetone → 4-methacryloyloxybutyl (E)-3-(4-hydroxyphenyl)acrylate

HRID 1735922Notes

Reaction equation

HRID 1735922 reaction equation
C(OC([O:6][C:7]1[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23](=[O:27])[C:24]([CH3:26])=[CH2:25])=[O:16])=[CH:9][CH:8]=1)=O)C.CC(C)=O.N>N1C=CC=CC=1>[OH:6][C:7]1[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23](=[O:27])[C:24]([CH3:26])=[CH2:25])=[O:16])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 222AmmoniaHCID 220777024-methacryloyloxybutyl (E)-3-(4-ethoxycarbonyloxyphenyl)acrylate

Product 1

HCID 220777254-methacryloyloxybutyl (E)-3-(4-hydroxyphenyl)acrylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5 g of 4-methacryloyloxybutyl (E)-3-(4-ethoxycarbonyloxyphenyl)acrylate were dissolved in 40 ml of pyridine and treated at room temperature with a mixture of 60 ml of acetone and 7 ml of 25% aqueous ammonia solution. The reaction mixture was stirred at room temperature for 12 hours. After distillation of the acetone the mixture was neutralized with 2N hydrochloric acid, diluted with 100 ml of water and subsequently extracted 3 times with 100 ml of diethyl ether each time. The combined organic phases were dried over sodium sulphate, filtered and concentrated. Chromatographic purification of the residue on silica gel with hexane/ethyl acetate (vol. 7:3) gave 4-methacryloyloxybutyl (E)-3-(4-hydroxyphenyl)acrylate.

Workup

  1. distillationAfter distillation of the acetone the mixture
  2. additiondiluted with 100 ml of water
  3. extractionsubsequently extracted 3 times with 100 ml of diethyl ether each time
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customChromatographic purification of the residue on silica gel with hexane/ethyl acetate (vol. 7:3)

Sources & evidence

ORD record
ord-f1ca66dd50134bf3bf68154c1f26781c
Source dataset
uspto-grants-1996_07
Patent number
US05539074

Reaction notes

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