p-Toluenesulfonic acid monohydrate → HCID 178421825, compound

HRID 1836909Notes

Reaction equation

HRID 1836909 reaction equation
[Br:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:8]([CH3:14])([CH3:13])[C@@H:7]([OH:15])[C@@H:6]([OH:16])[C:5]([CH3:18])([CH3:17])[C:4]=2[CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>COC(OC)(C)C>[CH2-:6][C:7]([CH3:8])=[O:15].[Br:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:8]([CH3:14])([CH3:13])[C@@H:7]([OH:15])[C@@H:6]([OH:16])[C:5]([CH3:18])([CH3:17])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 69155444HCID 69155444, compound

Product 1

HCID 178421825HCID 178421825, compoundYield 199%

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Procedure

A solution of 7.73 g (24.7 mmol) of 2-bromo-cis-6,7-dihydroxy-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene and 445 mg (2.39 mmol) of p-toluenesulfonic acid monohydrate in 100 ml 2,2-dimethoxypropane was heated to reflux for 90 minutes. Upon cooling the resulting solution was partitioned between ethyl acetate and dilute aqueous sodium bicarbonate. The organic layer was washed with brine, dried over anhydrous sodium bicarbonate, and concentrated in vacuo to yield 9.10 g of 2-bromo-cis-6,7-dihydroxy-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene acetonide (M+=352) which was used without further purification.

Workup

  1. temperatureto reflux for 90 minutes
  2. temperatureUpon cooling the resulting solution
  3. customwas partitioned between ethyl acetate and dilute aqueous sodium bicarbonate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium bicarbonate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ea8e1ef334ec45ca967324bea5ed49f4
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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