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

HRID 1063872

반응식

HRID 1063872 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-cc32e226d4524a23a27f31ed755d1149
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06967220B2

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