Ammonium Chloride → 4-(Hydroxymethyl)-2-methylphenol

HRID 1269596

反応式

HRID 1269596 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:10].[B-].CCCC[N+](CCCC)(CCCC)CCCC.[Cl-].[NH4+]>C(Cl)Cl>[OH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([OH:1])=[C:3]([CH3:10])[CH:4]=1

参加物

5

反応物 3

HCID 25517Ammonium Chloride2 回HCID 1399014-Hydroxy-3-methylbenzaldehydeHCID 9881569Tetra-N-butylammonium borohydride

生成物 1

HCID 142518564-(Hydroxymethyl)-2-methylphenol収率 78.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 4-hydroxy-3-methylbenzaldehyde (10 g, 73.5 mmol) in dry CH2Cl2 (550 mL) under nitrogen at 5° C. was added tetra-N-butylammonium borohydride (20.58 g, 80 mmol) and the resultant mixture stirred for 1.25 h at 5° C. Saturated ammonium chloride solution (30 mL) was added to the reaction mixture and the resultant mixture stirred for 1 h at 5° C. Saturated ammonium chloride solution (60 mL) was added and the reaction mixture extracted with CH2Cl2, dried (Na2SO4) and the solvents removed in vacuo. Purification by flushing through silica (2×150 g) eluting with EtOAc afforded the title compound as an oily yellow solid (8.01 g).

後処理

  1. extractionthe reaction mixture extracted with CH2Cl2
  2. dry with materialdried (Na2SO4)
  3. customthe solvents removed in vacuo
  4. customPurification
  5. customby flushing through silica (2×150 g)
  6. washeluting with EtOAc

出典と根拠

ORDレコード
ord-65f961eafc8b4085a7dad5f5dd583874
出典データセット
uspto-grants-2007_04
特許番号
US07199239B2

関連ノート

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