Water → HCID 18314126, compound

HRID 277181Notes

Reaction equation

HRID 277181 reaction equation
[C:1](=[O:4])([O-])[O-].[Na+].[Na+].[OH2:7].Br[CH2:9][C:10]1[CH:11]=[CH:12][C:13]2[C:14]([CH3:25])([CH3:24])[CH2:15][CH2:16][C:17]([CH3:23])([CH3:22])[C:18]=2[C:19]=1CBr>O1CCOCC1>[OH:7][CH2:9][C:10]1[CH:11]=[CH:12][C:13]2[C:14]([CH3:25])([CH3:24])[CH2:15][CH2:16][C:17]([CH3:23])([CH3:22])[C:18]=2[C:19]=1[CH2:1][OH:4]

Participants

5

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 56976379HCID 56976379, compound

Product 1

HCID 18314126HCID 18314126, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

50 g of sodium carbonate was added at room temperature to a mixed solution of 400 ml water and 400 ml dioxane containing 10 g of the unpurified 3,4-dibromomethyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene, and the mixture was heated under reflux for 11 hours. The dioxane was removed, and then the residue was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and then evaporated. The resulting residue was subjected to silica gel column chromatography to give 1.6 g of the title compound as a yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 11 hours
  3. customThe dioxane was removed
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-27c9faa150964e6e8aecdd11135d37db
Source dataset
uspto-grants-2002_03
Patent number
US06355669B1

Reaction notes

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