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

HRID 1836797

Reaction equation

HRID 1836797 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b1548f03209b4fb5bb7bd38971776b78
Source dataset
uspto-grants-2004_08
Patent number
US06777578B2

Linked notes

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