Water → HCID 19369854, compound

HRID 849031Notes

Reaction equation

HRID 849031 reaction equation
[Br:1]Br.[C:3]([O:6][C:7]1[C:12]([CH3:13])=[C:11]([CH2:14][C:15]([CH3:17])=[CH2:16])[C:10]([OH:18])=[C:9]([O:19][CH3:20])[C:8]=1[O:21][CH3:22])(=[O:5])[CH3:4].C([O-])(=O)C.[Na+].O>C(O)(=O)C>[C:3]([O:6][C:7]1[C:8]([O:21][CH3:22])=[C:9]([O:19][CH3:20])[C:10]2[O:18][C:15]([CH2:17][Br:1])([CH3:16])[CH2:14][C:11]=2[C:12]=1[CH3:13])(=[O:5])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 517045Sodium AcetateHCID 19369853HCID 19369853, compound

Product 1

HCID 19369854HCID 19369854, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (1.9 g) was added to a solution (40 ml) of 4-acetoxy-2,3-dimethoxy-5-methyl-6-(2-methyl-2-propenyl)phenol (3.0 g) and sodium acetate (1.0 g) in acetic acid, and the mixture was stirred at room temperature for 30 minutes. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=85:15 to 4:1) to obtain the title compound (2.5 g, 65%) as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=85:15 to 4:1)

Sources & evidence

ORD record
ord-ddc2da1ebd704a66bafb34e742eb0dc7
Source dataset
uspto-grants-2000_01
Patent number
US06011046

Reaction notes

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