Acetic Acid → Ethyl 3-(4-cyano-3-hydroxyphenyl)propanoate

HRID 1937780노트

반응식

HRID 1937780 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][C:4]=1[O:16]C)#[N:2].[C-]#N.[Na+].CC(O)=O>CS(C)=O.O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][C:4]=1[OH:16])#[N:2]

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 22461741Ethyl 3-(4-cyano-3-methoxyphenyl)propionate

생성물 1

HCID 9834402Ethyl 3-(4-cyano-3-hydroxyphenyl)propanoate

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
160 °C

실험 절차

A mixture of ethyl 3-(4-cyano-3-methoxyphenyl)propionate (3.17 g, 13.6 mmol, 1 equiv) and sodium cyanide (2.00 g, 40.8 mmol, 3.00 equiv) in DMSO (60 mL) was stirred at 140-180° C. for 2 h. After 2.5 hours the reaction mixture was taken up in H2O (300 mL), adjusted to pH 7 with AcOH (2.1 mL), and extracted with Et2O (1×150 mL). The organic layer was washed with H2O (2×50 mL), dried (anh. Na2SO4), and concentrated (75° C.). This yielded 2.05 g (68.8%) of ethyl 4-(4-cyano-3-hydroxyphenyl)propionate as a light yellow crystalline solid: 1H-NMR (CDCl3) 7.42 (1H, d), 7.40 (1H, br s), 6.92 (1H, d), 6.81 (1H, dd), 4.15 (2H, q), 2.94 (2H, dd), 2.64 (2H, dd), 1.25 (3H, t).

후처리

  1. extractionextracted with Et2O (1×150 mL)
  2. washThe organic layer was washed with H2O (2×50 mL)
  3. dry with materialdried (anh. Na2SO4)
  4. concentrationconcentrated (75° C.)

출처 및 근거

ORD 기록
ord-0be0cba3c0134771b61f78e1ebfd5c3f
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06395919B1

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