Allyl bromide → Methyl 2-hydroxy-4-[(prop-2-en-1-yl)oxy]benzoate

HRID 29643

反応式

HRID 29643 の反応式
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[CH:20]=[CH2:21]>CC(C)=O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:21][CH:20]=[CH2:19])=[CH:6][C:5]=1[OH:11]

参加物

5

反応物 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 16523Methyl 2,4-Dihydroxybenzoate

生成物 1

HCID 13019278Methyl 2-hydroxy-4-[(prop-2-en-1-yl)oxy]benzoate収率 77%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a solution of 2,4-dihydroxy-benzoic acid methyl ester (12.254 g, 72.8 mmol) in acetone (120 mL) was added potassium carbonate (30.72 g, 222.3 mmol) and allyl bromide (7 mL, 80.9 mmol). The reaction mixture was heated at reflux for 5 hours, and then cooled to room temperature. It was partitioned between ethyl acetate and brine and the aqueous layer was extracted with ethyl acetate. The combined organics were washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/hexanes (4/96) to afford 4-allyloxy-2-hydroxy-benzoic acid methyl ester (10.952 g, 77%) as a yellow oil. 1H NMR (300 MHz, CDCl3); δ 10.95 (s, 1H), 7.72 (d, 2H), 6.45 (m, 2H), 6.02 (m, 1H), 5.35 (m, 2H), 4.55 (d, 2H), 3.90 (s, 3H).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 5 hours
  3. customIt was partitioned between ethyl acetate and brine
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organics were washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-7fced78c4df249e9ac3f703c112a78d0
出典データセット
uspto-grants-2008_09
特許番号
US07420083B2

関連ノート

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