Dimethyl Sulfate → 4-(2',5'-Dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenol

HRID 1789598Notes

Reaction equation

[OH:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[C:5](O)=[C:4]([CH3:11])[C:3]=1[CH2:12][CH:13]=[C:14]([CH3:17])CO.[OH-].[Na+].[C:20](=[O:23])([O-])[O-].[K+].[K+].S([O:31][CH3:32])(OC)(=O)=O.[Br-].[C:34]([NH3+])(C)(C)C>O.C(Cl)Cl>[CH3:34][O:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[C:5]([O:31][CH3:32])=[C:4]([CH3:11])[C:3]=1[CH2:12][CH:13]=[C:14]([CH3:17])[CH2:20][OH:23]

Participants

Conditions

Temperature: 30 °C

Procedure

A mixture of 3.0 g of 4-(2',5'-dihydroxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenol, 40 ml of methylene chloride, 6 ml of water, 5.6 g of sodium hydroxide, 0.6 g of potassium carbonate, 1.6 g of dimethyl sulphate and 0.25 g of tert.butylammonium bromide is stirred well at 30° C. under argon for 3 hours and thereafter poured into water. The aqueous mixture is extracted with diethyl ether, and the ether phase is washed in sequence with sodium bicarbonate solution and sodium chloride solution, dried over anhydrous sodium sulphate and evaporated to dryness. From the residue (3.7 g) there are obtained by column chromatography (silica gel, diethyl ether/n-hexane) 1.6 g of 4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenol in the form of white crystals, m.p. 87°-88° C.

Workup

extractionThe aqueous mixture is extracted with diethyl ether
washthe ether phase is washed in sequence with sodium bicarbonate solution and sodium chloride solution
dry with materialdried over anhydrous sodium sulphate
customevaporated to dryness

Sources & evidence

ORD record: ord-6ee95f6e6ecf4cd4a00b3665941096fd
Source dataset: uspto-grants-1987_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04689427

Reaction notes

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