Methyl phenylacetate → HCID 67917566, compound

HRID 1885798Notes

Reaction equation

HRID 1885798 reaction equation
[C:1]1([CH2:7][C:8]([O:10][CH3:11])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:14](=O)([O-])[O-:15].[Na+].[Na+]>C(OC)=O.CN(C=O)C>[OH:15][CH:14]=[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

6

Reactant 3

HCID 7559Methyl phenylacetateHCID 10340Sodium CarbonateHCID 24758Sodium hydride

Product 1

HCID 67917566HCID 67917566, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 7865Methyl formateSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of methyl phenylacetate (16.03g) in methyl formate (132ml) and dry DMF (100 ml) was added dropwise over 40 minutes to a stirred suspension of sodium hydride (5.14g) in dry DMF (200ml) at between 0° and 5° C. (effervescence and foaming). The resulting mixture was stirred at about -5° C. for 30 minutes, diluted with dry DMF (250ml), then allowed to warm and stir at room temperature for 3 hours. Ice and sodium carbonate were added to the mixture and it was washed with ether (x2), then acidified with concentrated hydrochloric acid and extracted with ether (x4). The extracts were washed with water (x3), treated with magnesium sulphate and charcoal, filtered and concentrated to give methyl 3-hydroxy-2-phenylpropenoate (13.56g, 71%) as a solid, m.p. 33.5°-35.5° C., which was used for the subsequent steps without further purification.

Workup

  1. temperatureto warm
  2. stirringstir at room temperature for 3 hours
  3. washwas washed with ether (x2)
  4. extractionextracted with ether (x4)
  5. washThe extracts were washed with water (x3)
  6. additiontreated with magnesium sulphate and charcoal
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9a8b399dc2cc4d2ca863a9031732fc22
Source dataset
uspto-grants-1992_09
Patent number
US05145954

Reaction notes

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