Water → Methyl 3-Methoxy-2-naphthoate

HRID 78294ノート

反応式

HRID 78294 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 296952Methyl 3-Methoxy-2-naphthoate収率 95.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-1059a2819a40496699b47cc78ef555db
出典データセット
uspto-grants-2014_09
特許番号
US08841330B2

反応ノート

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