Dimethyl Sulfate → 7-Methoxy-2-naphthol

HRID 883597

反応式

HRID 883597 の反応式
[OH-].[Na+].S([O:8][CH3:9])(OC)(=O)=O.[OH:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][C:15](O)=[CH:16][CH:17]=2)[CH:12]=1>ClCCl.O>[OH:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][C:15]([O:8][CH3:9])=[CH:16][CH:17]=2)[CH:12]=1

参加物

6

反応物 3

HCID 6497Dimethyl Sulfate2 回HCID 113972,7-NaphthalenediolHCID 14798Sodium Hydroxide2 回

生成物 1

HCID 8531737-Methoxy-2-naphthol収率 30.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

Sodium hydroxide (20 ml, 1M) and dimethyl sulfate (15.0 ml, 158 mmol) were added dropwise to a solution of 2,7-dihydroxynaphthalene (6.6 g, 40 mmol) in dichloromethane (100 ml) and water (60 ml). Additional sodium hydroxide (20 ml, 1M) and dimethyl sulfate (15.0 ml, 158 mmol) were added and the resulting mixture was stirred at room temperature for 2 hours. The two phases were separated and the aqueous layer was extracted with dichloromethane twice. The combined organic extracts were washed with 1 M HCl, dried over magnesium sulfate and concentrated under vacuum. The crude material was purified by column chromatography (5:1 heptane/ethyl acetate) to give 2-hydroxy-7-methoxynaphthalene (2.1 g, 30%, 100% AUC HPLC): 1H NMR (300 MHz, CDCl3) δ 7.66-7.70 (m, 2H), 6.94-7.08 (m, 4H), 4.90 (s, 1H), 3.92 (s, 3H).

後処理

  1. customThe two phases were separated
  2. extractionthe aqueous layer was extracted with dichloromethane twice
  3. washThe combined organic extracts were washed with 1 M HCl
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe crude material was purified by column chromatography (5:1 heptane/ethyl acetate)

出典と根拠

ORDレコード
ord-c4540ba3fa7444ad99a0695efb7ce8df
出典データセット
uspto-grants-2012_08
特許番号
US08236796B2

関連ノート

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