Acetylresorcinol → 3-Benzyloxyphenyl acetate

HRID 482077

반응식

HRID 482077 반응식
[C:1]([O:4][C:5]1[CH:11]=[CH:10][CH:9]=[C:7]([OH:8])[CH:6]=1)(=[O:3])[CH3:2].[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C>[C:1]([O:4][C:5]1[CH:11]=[CH:10][CH:9]=[C:7]([O:8][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=1)(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 5055AcetylresorcinolHCID 7498Benzyl BromideHCID 24758Sodium hydride

생성물 1

HCID 223458653-Benzyloxyphenyl acetate수율 55%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

Resorcinol monoacetate (6.10 g, 40 mmol) in DMF (10 mL) was added dropwise to a mixture of NaH (95%, 0.92 g, 40 mmol) in DMF (50 mL). The reaction mixture was stirred at room temperature for 10 min. Benzyl bromide (6.85 g, 40 mmol) in DMF (10 mL) was added dropwise and stirring was continued at room temperature for 2 h. The reaction was quenched carefully with water (100 mL) and then extracted with ethyl acetate (3×100 mL). The organic phase was washed with brine (2×50 mL), dried over Na2 SO4, and concentrated in vacuo. The residue was then purified by flash column chromatography (1:1 hexane:methylene chloride) to give the title compound as a white solid (5.30 g, 55%). 1H-NMR (300 MHz, CDCl3) δ 2.28 (s, 3H), 5.03 (s, 2H), 6.72 (m, 2H), 6.85 (dd, 1H), 7.27 (t, 1H), 7.41 (m, 5H).

후처리

  1. stirringstirring
  2. waitwas continued at room temperature for 2 h
  3. customThe reaction was quenched carefully with water (100 mL)
  4. extractionextracted with ethyl acetate (3×100 mL)
  5. washThe organic phase was washed with brine (2×50 mL)
  6. customdried over Na2 SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was then purified by flash column chromatography (1:1 hexane:methylene chloride)

출처 및 근거

ORD 기록
ord-7c40cba6b854474296734844174ab641
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05792769

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