Methyl 4-(benzyloxy)-3,5-dichlorobenzoate → (4-Benzyloxy-3,5-dichlorophenyl)methanol

HRID 901143ノート

反応式

HRID 901143 の反応式
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([Cl:19])[CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:12]([O:11][C:7]1[C:6]([Cl:19])=[CH:5][C:4]([CH2:3][OH:2])=[CH:9][C:8]=1[Cl:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

4

反応物 2

HCID 16749549Methyl 4-(benzyloxy)-3,5-dichlorobenzoateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 16749116(4-Benzyloxy-3,5-dichlorophenyl)methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 4-benzyloxy-3,5-dichloro-benzoic acid methyl ester (CAB02115, 7.20 g, 23.14 mmol) in THF (20 mL) was added slowly with a syringe to a suspension of lithium aluminium hydride (1.50 g, 39.5 mmol) in THF (40 mL). The reaction mixture was stirred for 30 minutes at room temperature and then carefully quenched by addition of 2N sodium hydroxide solution in water. After 20 minutes stirring the colour of the mixture turned from grey to white. The white precipitate was filtered off, the filtrate was dried over sodium sulphate and concentrated under reduced pressure. The residue was recrystallised from dichloromethane/hexane. Yield: 5.83 g (89%) white powder. 1H-NMR (400 MHz, CDCl3) δ=1.85 (t, J=5.9 Hz, 1H, —OH), 4.63 (d, J=5.9 Hz, 2H), 5.04 (s, 2H), 7.33 (s, 2H), 7.35-7.44 (m, 3H), 7.55-7.59 (m, 2H). 13C-NMR (100 MHz, CDCl3) δ=64.05, 75.03, 127.36, 128.70, 128.75, 129.91, 136.39; 138.64, 150.32.

後処理

  1. customcarefully quenched by addition of 2N sodium hydroxide solution in water
  2. stirringAfter 20 minutes stirring the colour of the mixture
  3. filtrationThe white precipitate was filtered off
  4. dry with materialthe filtrate was dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallised from dichloromethane/hexane

出典と根拠

ORDレコード
ord-e3cad6ba7f404f8a8f1f57331cd5807e
出典データセット
uspto-grants-2008_04
特許番号
US07361677B2

反応ノート

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