Water → Methyl 3-Methoxy-2-naphthoate

HRID 78294

반응식

HRID 78294 반응식
[OH:1][C:2]1[C:3]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:16]([O-])([O-])=O.[K+].[K+].IC.O>CN(C=O)C>[CH3:16][O:1][C:2]1[C:3]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 70163Methyl 3-hydroxy-2-naphthoate

생성물 1

HCID 296952Methyl 3-Methoxy-2-naphthoate수율 95.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A slurry of methyl 3-hydroxy-2-naphthoate (10.1 g, 50.1 mmol) and K2CO3 (7.96 g, 57.6 mmol) in DMF (200 mL) was stirred at room temp. for 15 min., then treated with iodomethane (3.43 mL, 55.1 mmol). The mixture was allowed to stir at room temp. overnight, then was treated with water (200 mL). The resulting mixture was extracted with EtOAc (2×200 mL). The combined organic layers were washed with a saturated NaCl solution (100 mL), dried (MgSO4), concentrated under reduced pressure (approximately 0.4 mmHg overnight) to give methyl 3-methoxy-2-naphthoate as an amber oil (10.30 g): 1H-NMR (DMSO-d6) δ 2.70 (s, 3H), 2.85 (s, 3H), 7.38 (app t, J=8.09 Hz, 1H), 7.44 (s, 1H), 7.53 (app t, J=8.09 Hz, 1H), 7.84 (d, J=8.09 Hz, 1H), 7.90 (s, 1H), 8.21 (s, 1H).

후처리

  1. extractionThe resulting mixture was extracted with EtOAc (2×200 mL)
  2. washThe combined organic layers were washed with a saturated NaCl solution (100 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure (approximately 0.4 mmHg overnight)

출처 및 근거

ORD 기록
ord-1059a2819a40496699b47cc78ef555db
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841330B2

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