Methyl phenylacetate → HCID 67917566, 화합물

HRID 1885798노트

반응식

HRID 1885798 반응식
[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]

참가 물질

6

반응물 3

HCID 7559Methyl phenylacetateHCID 10340Sodium CarbonateHCID 24758Sodium hydride

생성물 1

HCID 67917566HCID 67917566, 화합물수율 71%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매3회HCID 7865Methyl formate용매

반응 조건

온도
-5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9a8b399dc2cc4d2ca863a9031732fc22
출처 데이터셋
uspto-grants-1992_09
특허 번호
US05145954

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