Ethylene Glycol → 2,2-Dimethyl-3-phenylpropanoic acid

HRID 432397ノート

反応式

HRID 432397 の反応式
[CH3:1][C:2]([CH3:12])([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]#N.[OH-:13].[K+].C(O)C[OH:17]>>[CH3:1][C:2]([CH3:12])([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:17])=[O:13]

参加物

4

反応物 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 118050482,2-Dimethyl-3-phenylpropanenitrile

生成物 1

HCID 218802,2-Dimethyl-3-phenylpropanoic acid収率 76%

反応条件

温度
196 °C

実験手順

A solution of 2,2-dimethyl-3-phenylpropanenitrile (1.0 g, 6.28 mmol) in ethylene glycol (5 mL) was treated with solid potassium hydroxide (1.06 g, 18.84 mmol). The reaction mixture was stirred for 48 h at 196° C. under a nitrogen atmosphere. Ethylene glycol was removed under vacuum distillation. 1 N Sodium hydroxide solution (25 mL) and ethyl acetate (15 mL) were added to the brown residue. The layers were separated, and the aqueous layer was extracted with ethyl acetate (375 mL). The combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered, and evaporated under reduced pressure to give 0.856 g (76%) of 2,2-dimethyl-3-phenylpropanoic acid. 1H NMR (DMSO-d6, 400 MHz) δ 12.20 (s, 1H), 7.28-7.24 (m, 2H), 7.22-7.20 (m, 1H), 7.15-7.13 (m, 2H), 2.78 (s, 2H), 1.07 (s, 6H). This compound was used in subsequent reaction with out further analysis.

後処理

  1. customEthylene glycol was removed under vacuum distillation
  2. addition1 N Sodium hydroxide solution (25 mL) and ethyl acetate (15 mL) were added to the brown residue
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (375 mL)
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-0b880b510097450a9408fea4d0f362d9
出典データセット
uspto-grants-2003_12
特許番号
US06660744B1

反応ノート

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