Hydrogen Peroxide → 3-Bromo-6-methoxybenzene-1,2-diol

HRID 1836797

反応式

HRID 1836797 の反応式
[OH:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[C:6]([Br:12])[C:3]=1C=O.[OH:13]O>[OH-].[Na+]>[Br:12][C:6]1[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:2]([OH:1])[C:3]=1[OH:13]

参加物

4

反応物 2

HCID 784Hydrogen Peroxide2 回HCID 2622376-Bromo-2-hydroxy-3-methoxybenzaldehyde

生成物 1

HCID 37058743-Bromo-6-methoxybenzene-1,2-diol収率 64.2%

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

実験手順

Aldehyde 12 (23 g) was suspended in 2% sodium hydroxide (300 mL) and a solution of 30% hydrogen peroxide (15.8 g, 1.4 eq.) was added. After 2 hours, another portion of 30% hydrogen peroxide (1.4 eq.) was added and the solution stirred overnight. The reaction mixture was acidified, extracted with dichloromethane, washed with sodium thiosulfate and the solvent removed in vacuo to afford a tan solid. The solid was recrystallized from methanol to afford colorless crystals (14 g, 64%): m.p. 122.3-124.3° C., lit20 m.p. 124-126° C.; EIMS m/z 220 (M+, 81Br), 218 (M+, 79Br), 205, 203, 177, 175, 95; 1HNMR δ 6.99 (1H, d, J=9.0 Hz, H5), 6.42 (1H, d, J=9.0 Hz, H4), 5.56 (1H, s, OH), 5.51 (1H, s, OH), 3.88 (3H, s, OCH3); 13C—NMR (75.5 MHZ) δ 146.59, 140.95, 133.47, 122.21, 104.35, 101.55, 56.31; Anal. Calcd. For C7H7O3Br: C, 38.39; H, 3.22. Found: C, 38.47; H, 3.36.

後処理

  1. extractionextracted with dichloromethane
  2. washwashed with sodium thiosulfate
  3. customthe solvent removed in vacuo
  4. customto afford a tan solid
  5. customThe solid was recrystallized from methanol

出典と根拠

ORDレコード
ord-b1548f03209b4fb5bb7bd38971776b78
出典データセット
uspto-grants-2004_08
特許番号
US06777578B2

関連ノート

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