Acetylresorcinol → 3-Benzyloxyphenyl acetate

HRID 482077

反応式

HRID 482077 の反応式
[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]

参加物

5

反応物 3

HCID 5055AcetylresorcinolHCID 7498Benzyl BromideHCID 24758Sodium hydride

生成物 1

HCID 223458653-Benzyloxyphenyl acetate収率 55%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-7c40cba6b854474296734844174ab641
出典データセット
uspto-grants-1998_08
特許番号
US05792769

関連ノート

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