Water → Ethyl 4-(benzyloxy)-2-hydroxy-6-methylbenzoate

HRID 2117194ノート

反応式

HRID 2117194 の反応式
[C:1](=[O:4])([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:15]([O:18][CH2:19][CH3:20])(=[O:17])[CH3:16].[OH2:21]>CC(C)=O>[CH2:19]([O:18][C:15](=[O:17])[C:16]1[C:13]([CH3:12])=[CH:8][C:9]([O:21][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:10][C:1]=1[OH:4])[CH3:20]

参加物

6

反応物 4

HCID 962WaterHCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate

生成物 1

HCID 14408138Ethyl 4-(benzyloxy)-2-hydroxy-6-methylbenzoate

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

Ethyl-2,4-dihydroxy-6-methyl benzoate (4 g, 21 mmol) is dissolved in acetone (80 mL) and to this solution is added potassium carbonate (2.9 g, 21 mmol) and benzyl bromide (2.5 mL, 21 mmol). This mixture is heated at reflux for 16 hours. To the cooled reaction is added ethyl acetate (100 mL) and water (100 mL). The organic layer is washed with water (2×80 mL) and brine (2×80 mL), then dried over magnesium sulfate and the solvent removed in vacuo. The crude is purified by column chromatography (silica, 10% ethyl acetate in hexanes) to give the title compound: 1H NMR (300 MHz, CDCl3) δ 7.38 (m, 5H), 6.41 (d, 1H), 6.38 (d, 1H), 5.05 (s, 2H), 4.40 (q, 2H), 2.51 (s, 3H), 1.40 (t, 3H).

後処理

  1. temperatureThis mixture is heated
  2. temperatureat reflux for 16 hours
  3. customTo the cooled reaction
  4. washThe organic layer is washed with water (2×80 mL) and brine (2×80 mL)
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent removed in vacuo
  7. customThe crude is purified by column chromatography (silica, 10% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-869ce93216e84b46b627c096e3cde571
出典データセット
uspto-grants-2008_10
特許番号
USRE040558E1

反応ノート

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