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

HRID 1937780ノート

反応式

HRID 1937780 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
160 °C

実験手順

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).

後処理

  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.)

出典と根拠

ORDレコード
ord-0be0cba3c0134771b61f78e1ebfd5c3f
出典データセット
uspto-grants-2002_05
特許番号
US06395919B1

反応ノート

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