Chloroform → 4-Methoxybenzhydryl alcohol

HRID 369920

反応式

HRID 369920 の反応式
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1.C(Cl)(Cl)Cl>CO>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([OH:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1

参加物

5

反応物 3

HCID 6212ChloroformHCID 691464-MethoxybenzophenoneHCID 4311764Sodium borohydride2 回

生成物 1

HCID 953754-Methoxybenzhydryl alcohol収率 99.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Solid NaBH4 (2.55 g, 0.067 mol) was added portion-wise to a solution of p-methoxybenzophenone (25.14 g, 0.118 mol) in MeOH (150 mL) at room temperature over 10 min. After the exothermic reaction had subsided, the reaction mixture was stirred at room temperature for 2 h. TLC (SiO2, CHCl3) indicated incomplete reaction; therefore, additional NaBH4 (2.55 g) was added and the reaction mixture was stirred at room temperature an additional 2 h. The MeOH was evaporated and the residue partitioned between water (100 mL) and CH2Cl2 (100 mL). The layers were separated, and the aqueous layer was extracted with CH2Cl2 (200 mL). The combined organic layers were dried (Na2SO4), filtered and evaporated to give the alcohol (25.24 g, 99%) as a white solid: m.p. 66-67° C. The structure was confirmed by 1H--NMR in CDCl3.

後処理

  1. customAfter the exothermic reaction
  2. customreaction
  3. stirringthe reaction mixture was stirred at room temperature an additional 2 h
  4. customThe MeOH was evaporated
  5. customthe residue partitioned between water (100 mL) and CH2Cl2 (100 mL)
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with CH2Cl2 (200 mL)
  8. dry with materialThe combined organic layers were dried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated

出典と根拠

ORDレコード
ord-b238aa7ed36048e395c3d404301797b7
出典データセット
uspto-grants-2000_10
特許番号
US06140137

関連ノート

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