Allyl bromide → 1-[2-(Allyloxy)-4-methylphenyl]ethanone

HRID 63957ノート

反応式

HRID 63957 の反応式
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[CH:19]=[CH2:20]>CN(C)C=O>[CH2:20]([O:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10])[CH:19]=[CH2:18]

参加物

5

反応物 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 813382'-Hydroxy-4'-methylacetophenone

生成物 1

HCID 607470631-[2-(Allyloxy)-4-methylphenyl]ethanone収率 98%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1-(2-hydroxy-4-methyl-phenyl)-ethanone (10 g, 67 mmol) in dimethylformamide (100 mL) was added potassium carbonate (18.4 g, 133 mmol), followed by allyl bromide (5.75 mL, 67 mmol). The reaction was stirred at room temperature for 16 hours. The residue was partitioned between ethyl acetate (200 mL) and water (800 mL), the organics were separated, and washed with brine (50 mL), dried over MgSO4 and concentrated in vacuo. After cooling the concentrate to room temperature the title compound crystallised as colourless platelets, 12.40 g, in a 98% yield. LCMS (2 min acidic) 1.20 min 72-100% pure by UV, ES+/AP+ 191. 1HNMR (400 MHz, CDCl3) δ ppm 2.37 (s, 3H), 2.63 (s, 3H), 4.61-4.66 (m, 2H), 5.33 (dq, 1H), 5.44 (dq, 1H), 6.10 (m, 1H), 6.76 (s, 1H), 6.80-6.83 (m, 1H), 7.68 (d, 1H).

後処理

  1. customThe residue was partitioned between ethyl acetate (200 mL) and water (800 mL)
  2. customthe organics were separated
  3. washwashed with brine (50 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. temperatureAfter cooling the
  7. concentrationconcentrate to room temperature the title compound
  8. customcrystallised as colourless platelets, 12.40 g, in a 98% yield
  9. customLCMS (2 min acidic) 1.20 min 72-100%

出典と根拠

ORDレコード
ord-75359a5b606c485db38b74db2ae643ea
出典データセット
uspto-grants-2016_09
特許番号
US09447116B2

反応ノート

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