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

HRID 1836797

반응식

HRID 1836797 반응식
[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]

참가 물질

4

반응물 2

HCID 784Hydrogen Peroxide2회HCID 2622376-Bromo-2-hydroxy-3-methoxybenzaldehyde

생성물 1

HCID 37058743-Bromo-6-methoxybenzene-1,2-diol수율 64.2%

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b1548f03209b4fb5bb7bd38971776b78
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06777578B2

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