3,5-Dichloro-4-hydroxybenzoic acid → Benzenemethanol, 3,5-dichloro-4-hydroxy-

HRID 1063872

反応式

HRID 1063872 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:12])[C:10]=1[OH:11])[C:5](O)=[O:6].B.C1COCC1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:8]=[C:9]([Cl:12])[C:10]=1[OH:11]

参加物

4

反応物 2

HCID 187493,5-Dichloro-4-hydroxybenzoic acidHCID 2723981Borane;tetrahydrofuran

生成物 1

HCID 176409Benzenemethanol, 3,5-dichloro-4-hydroxy-収率 99.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

To a solution of 3,5-dichloro-4-hydroxybenzoic acid (4.0 g, 19.3 mmol) in THF (60 ml) under argon was added borane-THF complex (39.0 mmol, 39.0 ml of 1 M solution in THF) dropwise. After addition, the reaction mixture was heated at 60° C. for 6 h, then quenched with water and extracted with ethyl acetate three times. The organic extract was washed with water, then brine, dried (sodium sulfate) and concentrated in vacuo to afford the title compound (3.7 g, 99%) as white solid. 1H NMR (400 MHz, CDCl3) δ 7.28 (s, 2H), 5.83 (s, 1H), 4.59 (s, 2H), MS: (M+1-H2O)=175

後処理

  1. additionAfter addition
  2. customquenched with water
  3. extractionextracted with ethyl acetate three times
  4. extractionThe organic extract
  5. washwas washed with water
  6. dry with materialbrine, dried (sodium sulfate)
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-cc32e226d4524a23a27f31ed755d1149
出典データセット
uspto-grants-2005_11
特許番号
US06967220B2

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