Dimethyl Sulfate → 7-Methoxy-2-naphthol

HRID 883597

반응식

HRID 883597 반응식
[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

참가 물질

6

반응물 3

HCID 6497Dimethyl Sulfate2회HCID 113972,7-NaphthalenediolHCID 14798Sodium Hydroxide2회

생성물 1

HCID 8531737-Methoxy-2-naphthol수율 30.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c4540ba3fa7444ad99a0695efb7ce8df
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236796B2

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