Reaction #82233

Reaction equation

methyl 6-hydroxymethyl-5,6,7,8-tetrahydro-2-naphthalenecarboxylate

2,3-dihydropyrane

2,3-dihydropyrane

→

methyl 6-[(2-tetrahydropyranyl)oxymethyl]-5,6,7,8-tetrahydro-2-naphthalenecarboxylate

Yield 99.3%

Solvents

diethyl ether

Conditions

Workup

1. 1
   workup.STIRRINGby stirring for 5 hours
2. 2
   OtherThe resulting reaction mixture
3. 3
   Washthe mixture was washed with saturated sodium bicarbonate aqueous solution, water and saturated sodium chloride aqueous solution in that order
4. 4
   Otherby drying
5. 5
   workup.DISTILLATIONBy distilling off the solvent

Procedure

10.0 g of methyl 6-hydroxymethyl-5,6,7,8-tetrahydro-2-naphthalenecarboxylate was added to 3.82 g of 2,3-dihydropyrane. After further adding 5 drops of concentrated sulfuric acid, the resulting mixture was stirred for 1 hour. To this were further added 1.00 g of 2,3-dihydropyrane and 3 drops of concentrated sulfuric acid, followed by stirring for 5 hours. The resulting reaction mixture was mixed with 100 ml of diethyl ether, and the mixture was washed with saturated sodium bicarbonate aqueous solution, water and saturated sodium chloride aqueous solution in that order, followed by drying. By distilling off the solvent, 13.72 g of methyl 6-[(2-tetrahydropyranyl)oxymethyl]-5,6,7,8-tetrahydro-2-naphthalenecarboxylate was obtained in the form of yellow oil.

Source