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

HRID 1781271Notes

Reaction equation

HRID 1781271 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15](=[CH:20][OH:21])[C:16]([O:18][CH3:19])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1/[C:15](=[CH:20]\[O:21][CH3:22])/[C:16]([O:18][CH3:19])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

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

Product 2

HCID 838698Methyl 2-(2-(benzyloxy)phenyl)-3-methoxyacrylateHCID 11076055Methyl 2-(2-(benzyloxy)phenyl)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The crude methyl 2-(2'-benzyloxyphenyl)-3-hydroxyacrylate 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 trituration with ether/petrol. Recrystallization from dry methanol afforded (E)-methyl 2-(2'-benzyloxyphenyl)-3-methoxyacrylate as a white, crystalline solid (5.44 g, 17% yield from methyl 2-benzyloxyphenylacetate), mp. 76°-77° C.; infrared max. (nuJol mull): 1710, 1640 cm-1 ; 1H nmr (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-b04a46ce4c88420bb722e57bd623063c
Source dataset
uspto-grants-1997_05
Patent number
US05633256

Reaction notes

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