Reaction #1227

Reaction equation

water

sodium hydride

methyl 2-hydroxy-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)benzoate

iodomethane

→

methyl 2-methoxy-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)benzoate

Solvents

DMF

DMF

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for two hours
2. 2
   Extractionextracted with ethyl ether
3. 3
   Otherthe organic phase decanted
4. 4
   Dryingdried over magnesium sulfate
5. 5
   Otherevaporated
6. 6
   Other1.6 g (96%) of the expected compound was recovered in the form of a colorless oil

Procedure

130 mg (4.2 mmol) of sodium hydride (80% in oil) and 20 ml of DMF were introduced into a three-necked flask, a solution of 1.6 g (4.2 mmol) of methyl 2-hydroxy-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)benzoate in 50 ml of DMF was added dropwise and the mixture was stirred until gaseous emission ceased. 340 μl (5.5 mmol) of iodomethane were then added and the mixture was stirred at room temperature for two hours. The reaction medium was poured into water, extracted with ethyl ether, the organic phase decanted, dried over magnesium sulfate and evaporated. 1.6 g (96%) of the expected compound was recovered in the form of a colorless oil.

Source