Bromine → HCID 13691074, compound

HRID 2290829Notes

Reaction equation

HRID 2290829 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH:11]([OH:18])[CH:12]([CH3:17])[CH2:13][CH2:14][CH2:15][CH3:16])[CH:5]=[CH:6][C:7]=1[OH:8].[Br:19]Br>C(O)(=O)C>[Br:19][C:5]1[CH:6]=[C:7]([OH:8])[C:2]([OH:1])=[CH:3][C:4]=1[CH2:9][CH2:10][CH:11]([OH:18])[CH:12]([CH3:17])[CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 13392878HCID 13392878, compound

Product 1

HCID 13691074HCID 13691074, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 0.5 g of 1-(3,4-dihydroxyphenyl)-4-methyl-3-octanol obtained in Example 1 in 20 ml of acetic acid was added dropwise a mixture of 0.37 g of bromine and 2 ml of acetic acid and after the color of bromine disappeared, the solvent was distilled off under reduced pressure. The residue thus formed was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was applied to silica gel column chromatography and eluted with a mixture of toluene and ethyl acetate (2:1) to provide 0.5 g of 1-(2-bromo-4,5-dihydroxyphenyl)-4-methyl-3-octanol.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. customThe residue thus formed
  3. extractionwas extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. washeluted with a mixture of toluene and ethyl acetate (2:1)

Sources & evidence

ORD record
ord-b9d7a7f956144183be567477bf1655f8
Source dataset
uspto-grants-1986_10
Patent number
US04618627

Reaction notes

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