Methanol → 2-(3-Methoxyphenyl)-2-methylpropanoic acid

HRID 1687824ノート

反応式

HRID 1687824 の反応式
[OH-:1].[K+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:11]([CH3:15])([CH3:14])[C:12]#N)[CH:8]=[CH:9][CH:10]=1.C[OH:17]>O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:11]([CH3:15])([CH3:14])[C:12]([OH:17])=[O:1])[CH:8]=[CH:9][CH:10]=1

参加物

5

反応物 3

HCID 887MethanolHCID 14797Potassium Hydroxide2 回HCID 101301932-(3-Methoxyphenyl)-2-methylpropanenitrile

生成物 1

HCID 108216342-(3-Methoxyphenyl)-2-methylpropanoic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
130 °C

実験手順

Into a round bottom flask, potassium hydroxide (35.4 g, 631 mmol) and water (225 mL, 12500 mmol) was added at 100° C. 2-(3-methoxy-phenyl)-2-methyl-propionitrile (44.20 g, 252.2 mmol) in Methanol (25.0 mL, 617 mmol) was added to the reaction mixture. The reaction was then heated to reflux at 130° C. over night. TLC suggested starting material. Potassium hydroxide (35.4 g, 631 mmoles) in water (50 mL) was added. The reaction was heated for 5 days. The reaction was partitioned with water (700 mL). The aqueous was acidified with concentrated HCl to pH 1. The solid was filtered and washed with water and EtOAc. The organic layer was separated. The aqueous was extracted with EtOAc (3×400 mL). The combined organic was washed with brine, and dried over MgSO4. The solid was then filtered and washed with EtOAc. The solvent was removed under vacuum to afford a brown oil. The oil was triturated with hexane to afford 2-(3-methoxy-phenyl)-2-methyl-propionic acid as a light yellow solid (36.2 g. 74%). H-NMR (DMSO-D6, 400 MHz): δ 12.30 (s, 1H), 7.24 (t, 1H), 6.90 (d, 1H), 6.75-6.88 (m, 2H), 3.74 (s, 3H), 1.45 (s, 6H)

後処理

  1. temperatureThe reaction was then heated
  2. temperatureThe reaction was heated for 5 days
  3. customThe reaction was partitioned with water (700 mL)
  4. filtrationThe solid was filtered
  5. washwashed with water and EtOAc
  6. customThe organic layer was separated
  7. extractionThe aqueous was extracted with EtOAc (3×400 mL)
  8. washThe combined organic was washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationThe solid was then filtered
  11. washwashed with EtOAc
  12. customThe solvent was removed under vacuum
  13. customto afford a brown oil
  14. customThe oil was triturated with hexane

出典と根拠

ORDレコード
ord-044104c248124cfb86e3eafcf377d2ee
出典データセット
uspto-grants-2012_04
特許番号
US08148391B2

反応ノート

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