Water → Methyl 2-(2-(benzyloxy)phenyl)-3-methoxyacrylate

HRID 1608152Notes

Reaction equation

HRID 1608152 reaction equation
[OH:1][CH:2]=[C:3]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:4]([O:6][CH3:7])=[O:5].[C:22](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.O>CN(C=O)C>[CH3:22][O:1]/[CH:2]=[C:3](\[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)/[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 69942437Methyl 2-(2'-benzyloxyphenyl)-3-hydroxyacrylate

Product 1

HCID 838698Methyl 2-(2-(benzyloxy)phenyl)-3-methoxyacrylateYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The crude methyl 3-hydroxy-2-(2'-benzyloxyphenyl)propenoate was dissolved in dry DMF (100 ml) and potassium carbonate (29.0 g) was added in one portion. Dimethyl sulphate (16.00 g) in dry DMF (10 ml) was then added dropwise with stirring. After ninety minutes, water (300 ml) was added and the solution was extracted with ether (2×300 ml). After washing with water (3×150 ml) and brine, the extracts were dried and concentrated under reduced pressure, and the resulting yellow oil solidified on trituation with ether/petrol. Recrystallization from dry methanol afforded E-methyl 3-methoxy-2-(2'-benzyloxyphenyl)propenoate as a white, crystalline solid (5.44 g, 17% yield from methyl 2-bemnzyloxyphenylacetate), M.P. 76°-77° C.; infrared maxima (nujol mull): 1710, 1640 cm-1 ; 1H nmr (CDCl3, 90 MHz): delta 3.63 (3H, s), 3.75 (3H, s), 5.05 (2H, s), 6.80-7.40 (9H, m), 7.50 (1H, s) ppm.

Workup

  1. waitAfter ninety minutes
  2. extractionthe solution was extracted with ether (2×300 ml)
  3. washAfter washing with water (3×150 ml) and brine
  4. customthe extracts were dried
  5. concentrationconcentrated under reduced pressure
  6. customRecrystallization from dry methanol

Sources & evidence

ORD record
ord-52bec39f016d4c1099147ec9ee64f81a
Source dataset
uspto-grants-1989_09
Patent number
US04870075

Reaction notes

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