Potassium Hydroxide → 4-(4-Hydroxy-3,5-diisopropylphenyl)butanoic acid

HRID 1056479ノート

反応式

HRID 1056479 の反応式
[OH:1][C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[CH:6][C:5]([C:11](=O)[CH2:12][CH2:13][C:14]([O:16]C)=[O:15])=[CH:4][C:3]=1[CH:19]([CH3:21])[CH3:20].[H][H].[OH-].[K+]>C(O)C.[Pd]>[OH:1][C:2]1[C:3]([CH:19]([CH3:21])[CH3:20])=[CH:4][C:5]([CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:6][C:7]=1[CH:8]([CH3:10])[CH3:9]

参加物

6

反応物 3

HCID 14797Potassium HydroxideHCID 19967177Methyl 4-(4-hydroxy-3,5-diisopropylphenyl)-4-oxobutanoateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 568512964-(4-Hydroxy-3,5-diisopropylphenyl)butanoic acid収率 91.7%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

Keto-ester 6 (1.0 g, 3.4 mmol) was dissolved in ethanol (50 mL) and palladium catalyst on charcoal (10%, 50 mg) was added. Hydrogenation was performed with 45 psi of hydrogen gas for 20 h. The catalyst was then filtered off and potassium hydroxide (909 mg, 16.2 mmol) was added, and the reaction mixture was refluxed for 1 h. The solvents were evaporated, and aqueous HCl (50 mL, 4.0 M) was added. The acidic aqueous phase was extracted with methylene chloride (3×30 mL), the combined organic extracts were dried over anhydrous magnesium sulfate and evaporated, giving 8 as white crystals (824 mg, 91%). 1H NMR (300 MHz, CDCl3): δ 6.89 (s, 2H), 3.18 (septet, J=6.9 Hz, 2H), 2.64 (t, J=7.7 Hz, 2H), 2.43 (t, J=7.4 Hz, 2H), 1.98 (q, J=7.7 Hz, 2H), 1.29 (d, J=6.9 Hz, 12H). 13C NMR (90.55 MHz, CDCl3): δ 180.51, 149.56, 134.07, 133.52, 123.83, 35.28, 33.98, 27.60, 27.09, 23.21. HRMS (m/z): [M+H]+ calcd. for C16H24O3 263.1653. found 263.1664.

後処理

  1. filtrationThe catalyst was then filtered off
  2. temperaturethe reaction mixture was refluxed for 1 h
  3. customThe solvents were evaporated
  4. additionaqueous HCl (50 mL, 4.0 M) was added
  5. extractionThe acidic aqueous phase was extracted with methylene chloride (3×30 mL)
  6. dry with materialthe combined organic extracts were dried over anhydrous magnesium sulfate
  7. customevaporated

出典と根拠

ORDレコード
ord-0232e8dde6fb41e58766c7f37fdbebc1
出典データセット
uspto-grants-2016_07
特許番号
US09399145B2

反応ノート

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