Water → p-(Benzyloxy)phenethyl alcohol

HRID 34405

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HRID 34405 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22](OC)=[O:23])=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(OCC)(=O)C.O>CCOCC>[CH2:7]([O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][OH:23])=[CH:19][CH:20]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2756645Methyl 2-(4-benzyloxyphenyl)acetateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 3017260p-(Benzyloxy)phenethyl alcohol

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

반응 조건

온도
0 °C

실험 절차

To a suspension of lithium aluminum hydride (10.8 g, 285 mmoles) in Et2O (300 mL) was very carefully added a solution of methyl 4-(benzyloxy)phenylacetate (6, 72.8 g, 284 mmoles) in Et2O (200 mL) over 40 minutes. After an additional 30 minutes, ethyl acetate (200 mL) was added, followed by H2O (500 mL) and the mixture maintained at 0° C. The mixture was then allowed to separate into two phases. The aqueous phase was extracted with Et2O (2×500 mL). The combined extracts were dried over anhydrous Na2SO4 and evaporated to yield 1-benzyloxy-4-(2-hydroxyethyl)benzene as a white solid, (7, 64.5 g, mp=85° C.). NMR (CDCl3)δppm: 7.33(s, 4H); 6.97(q, 4H); 4.97(s, 2H); 3.67(t, 3H); 4.43(t, 3H); 4.27(s, 1H). (Scheme II, Step 2.)

후처리

  1. customto separate into two phases
  2. extractionThe aqueous phase was extracted with Et2O (2×500 mL)
  3. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  4. customevaporated

출처 및 근거

ORD 기록
ord-f6e7e0fee778474390cb4d0cc375f17e
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04761420

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