2',4'-Dihydroxyacetophenone → 4'-Benzyloxy-2'-hydroxyacetophenone

HRID 858662

반응식

HRID 858662 반응식
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH:15][C:16]1[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:17]=1[C:23](=[O:25])[CH3:24]>CN(C=O)C>[CH2:7]([O:22][C:20]1[CH:19]=[CH:18][C:17]([C:23](=[O:25])[CH3:24])=[C:16]([OH:15])[CH:21]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

5

반응물 3

HCID 69902',4'-DihydroxyacetophenoneHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

생성물 1

HCID 3092574'-Benzyloxy-2'-hydroxyacetophenone수율 60.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Potassium carbonate (27.2 g, 0.2 mol) followed by benzyl bromide (7.04 mL, 59.2 mmol) were added to a solution of 1-(2,4-dihydroxy-phenyl)-ethanone (10 g, 66 mmol) in DMF (90 mL): The mixture was stirred for 2 hours and then partitioned between 1N HCl and EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated. Purification by flash column chromatography (0% to 20% EtOAc in hexanes) followed by recrystallization gave the title compound as a white solid (8.7 g, 55%). 1H NMR (400 MHz, CDCl3): δ 2.55 (s, 3 H), 5.09 (s, 2 H), 6.50 (s, 1 H), 6.51 (dd, J=9.1, 3.9 Hz, 1 H), 7.34–7.43 (m, 5 H), 7.64 (d, J=9.1 Hz, 1 H), 12.73 (s, 1 H).

후처리

  1. custompartitioned between 1N HCl and EtOAc
  2. washThe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (0% to 20% EtOAc in hexanes)
  6. customfollowed by recrystallization

출처 및 근거

ORD 기록
ord-fe87ee52d494475cb97c0477906d1d46
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07148226B2

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