Water → p-(Benzyloxy)phenethyl alcohol

HRID 34405

反応式

HRID 34405 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 3017260p-(Benzyloxy)phenethyl alcohol

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
0 °C

実験手順

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.)

後処理

  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

出典と根拠

ORDレコード
ord-f6e7e0fee778474390cb4d0cc375f17e
出典データセット
uspto-grants-1988_08
特許番号
US04761420

関連ノート

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