p-Toluenesulfonic acid monohydrate → HCID 178421825, compound
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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.