Phenol → Ethyl 2-(phenoxymethyl)prop-2-enoate

HRID 352708Notes

Reaction equation

HRID 352708 reaction equation
Br[CH2:2][C:3](=[CH2:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:10]1([OH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>C1COCC1>[O:16]([CH2:2][C:3](=[CH2:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 3106202-(Bromomethyl)acrylic acid ethyl ester

Product 1

HCID 13485949Ethyl 2-(phenoxymethyl)prop-2-enoateYield 80.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of ethyl 2-bromomethylacrylate (2.00 g, 10.4 mmol, ref: Villieras, J. and Rambaud, M. Synthesis, 1982, 914) and phenol(975 mg, 1.0 eq) in dry THF (20 mL) under N2 at 0° C. was treated with anhydrous K2CO3 (1.43 g, 1.0 mol eq). No reaction was observed for 1 h. Anhydrous DMF (20 mL) was added and stirred for 2 h at 0° C. and for 1 h at room temperature. After evaporation of DMF, water(100 mL) was added, and the reaction was extracted with ethyl acetate (100 mL×2). The organic extract was washed with brine (100 mL), dried (anh. Na2SO4), filtered and concentrated. Flash chromatography (40% CH2Cl2/hexanes) gave 1.712 g (80%) of the title compound.

Workup

  1. customAfter evaporation of DMF, water(100 mL)
  2. additionwas added
  3. extractionthe reaction was extracted with ethyl acetate (100 mL×2)
  4. extractionThe organic extract
  5. washwas washed with brine (100 mL)
  6. dry with materialdried (anh. Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-cb4fc2aafeb04d309337c2bd546c06df
Source dataset
uspto-grants-2004_06
Patent number
US06747050B1

Reaction notes

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