Acetic Acid → HCID 23498938, compound

HRID 1836896Notes

Reaction equation

HRID 1836896 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]([CH3:16])([CH3:15])[CH2:7][CH:8]([OH:14])[C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[Br:17]Br.[C:19]([OH:22])(=O)[CH3:20]>[Cl-].[Na+].O>[Br:17][C:3]1[C:2]([CH3:1])=[CH:11][C:10]2[C:9]([CH3:12])([CH3:13])[CH:8]([O:14][C:19](=[O:22])[CH3:20])[CH2:7][C:6]([CH3:16])([CH3:15])[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 231416HCID 231416, compound

Product 1

HCID 23498938HCID 23498938, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 4 g (18.3 mmol) of 3-methyl-6-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene in 20 mL of acetic acid was added 3.25 g (20.15 mmol) of bromine dropwise and the reaction was stirred at room temperature. After 16 hours, the reaction mixture was poured into brine and extracted with ethyl acetate. The organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution with hexane-15% ethyl acetate/hexane) to give 6 g (97%) of 2-bromo-3-methyl-6-acetoxy -5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene.(M+=338).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (gradient elution with hexane-15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ae21f55802e3484680d83671d99f171a
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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