Lithium Hydroxide → 4-(2-Tert-butoxycarbonyl-ethyl)-3,5-dimethyl-benzoic acid

HRID 1676121ノート

反応式

HRID 1676121 の反応式
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[C:6]([CH3:20])[CH:5]=1.[Li+].[OH-]>C(O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[C:16]([O:15][C:13]([CH2:12][CH2:11][C:7]1[C:8]([CH3:10])=[CH:9][C:4]([C:3]([OH:21])=[O:2])=[CH:5][C:6]=1[CH3:20])=[O:14])([CH3:19])([CH3:18])[CH3:17]

参加物

5

反応物 2

HCID 3939Lithium HydroxideHCID 669361734-(2-Tert-butoxycarbonyl-ethyl)-3,5-dimethyl-benzoic acid methyl ester

生成物 1

HCID 594979324-(2-Tert-butoxycarbonyl-ethyl)-3,5-dimethyl-benzoic acid収率 49.4%

試薬・触媒・溶媒 2

HCID 311Citric Acid溶媒HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

To a solution of 4-(2-tert-butoxycarbonyl-ethyl)-3,5-dimethyl-benzoic acid methyl ester (10.8 g, 37.0 mmol) in ethanol (100 mL) a 2 M aq. solution of LiOH (50 mL) is added at 0° C. The turbid mixture is stirred at 0° C. for 30 min, then at rt for 4 h. The mixture is diluted with 10% aq. citric acid solution and extracted three times with diethyl ether. The combined organic extracts are dried over MgSO4, filtered and concentrated. The solid residue is suspended in diethyl ether/heptane, stirred at rt, and filtered. The slurry procedure in diethyl ether/heptane is repeated. The solid material is collected and dried under HV to give 4-(2-tert-butoxycarbonyl-ethyl)-3,5-dimethyl-benzoic acid (5.09 g) as a white crystalline powder; LC-MS: tR=0.95 min, [M+1]+=279.14; 1H NMR (CDCl3): δ 1.47 (s, 9 H), 2.30-2.40 (m, 2 H), 2.39 (s, 6 H), 2.94-3.03 (m, 2 H), 7.75 (s, 2 H).

後処理

  1. waitat rt for 4 h
  2. extractionextracted three times with diethyl ether
  3. dry with materialThe combined organic extracts are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. stirringstirred at rt
  7. filtrationfiltered
  8. customThe solid material is collected
  9. customdried under HV

出典と根拠

ORDレコード
ord-003f94326edf4134b5e15827d22d4649
出典データセット
uspto-grants-2011_08
特許番号
US08003800B2

反応ノート

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