Water → HCID 22398226, compound

HRID 1070887Notes

Reaction equation

HRID 1070887 reaction equation
[CH3:1][C:2]1[C:3]([OH:16])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[Br:17]Br.O>C(O)(=O)C>[Br:17][C:4]1[C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=[C:2]([CH3:1])[C:3]=1[OH:16]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 2266903,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-ol

Product 1

HCID 22398226HCID 22398226, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 500 mL roundbottom flask, 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenol (10.2 g, 46.72 mmol) was dissolved in 100 mL Acetic Acid. To this solution Bromine (8.2 g, 51.39 mmol) was added. The reaction was stirred at room temperature for 20 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. The separated organic layer was washed with brine, dried over magnesium sulfate and concentrated. The crude product was purified by silica gel chromatography eluted with hexane to yield 1-Bromo-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenol (12.8 g, 92% yield).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe separated organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel chromatography
  6. washeluted with hexane

Sources & evidence

ORD record
ord-da2f84a0de6848c3ab705820fd245ada
Source dataset
uspto-grants-2005_06
Patent number
US06903132B2

Reaction notes

Loading…