Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → methyl(E)-3-(3-fluoro-4-hydroxyphenyl)acrylate

HRID 250834Notes

Reaction equation

HRID 250834 reaction equation
C1(P(=[CH:20][C:21]([O:23][CH3:24])=[O:22])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[OH:34])[CH:29]=O>C1(C)C=CC=CC=1.O>[F:25][C:26]1[CH:27]=[C:28](/[CH:29]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])[CH:31]=[CH:32][C:33]=1[OH:34]

Participants

5

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 5872503-Fluoro-4-hydroxybenzaldehyde

Product 1

HCID 67273036methyl(E)-3-(3-fluoro-4-hydroxyphenyl)acrylateYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

13.1 g (0.039 mol, 2.2 eq) of methyl (triphenylphosphoranylidene)acetate are added to a solution of 2.5 g (0.0178 mol, 1 eq) of 3-fluoro-4-hydroxybenzaldehyde in 30 ml of toluene. The reaction mixture is heated at 80° C. for 2 hours. The reaction medium is hydrolyzed in water and extracted with ethyl acetate. The organic phases are combined, washed with water and dried over sodium sulfate. The solvent is evaporated off and the oil obtained is chromatographed on silica gel (70/30 heptane/ethyl acetate). 2.7 g of methyl (E)-3-(3-fluoro-4-hydroxyphenyl)acrylate are obtained in solid form. Yield=78%

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is evaporated off
  5. customthe oil obtained
  6. customis chromatographed on silica gel (70/30 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-fdc3e6ec1a6d4b1584942ea9e128b919
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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