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

HRID 1676121노트

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HRID 1676121 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 311Citric Acid용매HCID 702Ethanol용매

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-003f94326edf4134b5e15827d22d4649
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003800B2

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