Methyl formate → Methyl 3-hydroxy-2-(3'-phenylphenoxy)propenate

HRID 483984Notes

Reaction equation

HRID 483984 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH:16]=[CH:17][CH:18]=2)[O:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:19](OC)=[O:20].[H-].[Na+]>CN(C=O)C>[OH:20][CH:19]=[C:11]([O:10][C:9]1[CH:16]=[CH:17][CH:18]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 7865Methyl formateHCID 24758Sodium hydrideHCID 13787157Methyl(3-phenylphenoxy)acetate

Product 1

HCID 67855452Methyl 3-hydroxy-2-(3'-phenylphenoxy)propenateYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Methyl (3-phenylphenoxy)acetate (6.0 g) and methyl formate (30.2 ml) were dissolved in DMF and added dropwise with stirring to a suspension of sodium hydride (1.44 g, 50% dispersion in oil) in DMF at 0° C. (ice-bath). After 45 minutes, the ice-bath was removed and the reaction mixture was stirred for 2 hours at room temperature. Aqueous sodium carbonate was then added. The aqueous layer was washed with ether, acidified to pH 4-5 with concentrated hydrochloric acid and then re-extracted with ether. The combined organic layers were washed with brine, dried, filtered and evaporated to give methyl 3-hydroxy-2-(3'-phenylphenoxy)propenoate as a pale yellow oil (6.05 g, 90% yield).

Workup

  1. additionadded dropwise
  2. customthe ice-bath was removed
  3. additionAqueous sodium carbonate was then added
  4. washThe aqueous layer was washed with ether
  5. extractionre-extracted with ether
  6. washThe combined organic layers were washed with brine
  7. customdried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-ef2b4ca0372f491794be2f601a351ff8
Source dataset
uspto-grants-1993_07
Patent number
US05229393

Reaction notes

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