Water → HCID 12366402, compound

HRID 437839Notes

Reaction equation

HRID 437839 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:10](=[CH:11][C:12]=1[CH3:13])[C:8](=[O:9])[CH:7]=[CH:6][C:5]2=[O:14].[Br:15]Br.C([O-])(=O)C.[Na+].O>C(O)(=O)C>[Br:15][C:6]1[C:5]([C:4]2[C:10]([C:8](=[O:9])[CH:7]=1)=[CH:11][C:12]([CH3:13])=[C:2]([CH3:1])[CH:3]=2)=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 2463546,7-dimethyl-1,4-naphthoquinoneHCID 517045Sodium Acetate

Product 1

HCID 12366402HCID 12366402, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 6,7-dimethyl naphtho-1,4-quinone (20.0 g.; 0.107 mole) in glacial acetic acid (250 ml) was stirred during the dropwise addition of bromine (5.6 ml; 17.2 g; 0.107 mole) in acetic acid (10 ml.) at 15° C. and allowed to stir at this temperature for a further 2 hours. Anhydrous sodium acetate (20 g) was added and the mixture stirred at 100° C. for 11/2 hours after an initial half hour period at room temperature; cooled, poured into water (2.5 l) and the yellow bromo product filtered off. It had m.p. (ethanol, chloroform) 156°-159° C. (Found; C, 53.47; H, 3.39; Br, 30.23; C12H9BrO2 requires; C, 54.36; H, 3.42; Br, 30.14%):

Workup

  1. stirringthe mixture stirred at 100° C. for 11/2 hours after an initial half hour period at room temperature
  2. temperaturecooled
  3. filtrationthe yellow bromo product filtered off
  4. custom(ethanol, chloroform) 156°-159° C. (Found; C, 53.47; H, 3.39; Br, 30.23; C12H9BrO2 requires; C, 54.36; H, 3.42; Br, 30.14%)

Sources & evidence

ORD record
ord-eac4f54b73684cacbfc0041ca0caefb9
Source dataset
uspto-grants-1977_06
Patent number
US04032544

Reaction notes

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