Réaction #1063524

Équation de réaction

5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthol

sodium hydride

chloromethyl methyl ether

sodium hydrogencarbonate

→

title compound

Rendement 106.9%

5,6,7,8-Tetrahydro-2-methoxymethoxy-5,5,8,8-tetramethylnaphthalene

Rendement 106.9%

Solvants

N,N-dimethylformamide

N,N-dimethylformamide

N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   Températurecooled to 0° C.
2. 2
   workup.ADDITIONfollowed by the addition
3. 3
   TempératureThe temperature of the mixture was gradually raised to room temperature (in 10 minutes)
4. 4
   workup.STIRRINGThe resulting mixture was further stirred for one hour
5. 5
   workup.ADDITIONfollowed by the addition
6. 6
   ExtractionThe obtained mixture was extracted with ethyl acetate
7. 7
   LavageThe organic phase was washed with a saturated aqueous solution of common salt
8. 8
   Séchagedried over anhydrous magnesium sulfate
9. 9
   workup.DISTILLATIONdistilled
10. 10
    Autreto remove the solvent
11. 11
    AutreThe residue was purified by silica gel chromatography (developer: 5% ethyl acetate/n-hexane)

Mode opératoire

10 ml of a solution of 4.0 g of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthol in N,N-dimethylformamide was dropwise added to 70 ml of a suspension of 1.01 g of sodium hydride (604 solution in oil) in anhydrous N,N-dimethylformamide at 0° C. The obtained mixture was stirred at room temperature for one hour and cooled to 0° C., followed by the addition thereto of 5 ml of a solution of 2.36 g of chloromethyl methyl ether in N,N-dimethylformamide. The temperature of the mixture was gradually raised to room temperature (in 10 minutes). The resulting mixture was further stirred for one hour, followed by the addition thereto of 30 ml of a saturated aqueous solution of sodium hydrogencarbonate. The obtained mixture was extracted with ethyl acetate. The organic phase was washed with a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and distilled to remove the solvent. The residue was purified by silica gel chromatography (developer: 5% ethyl acetate/n-hexane) to give 5.2 g of the title compound as a colorless oil. 1H-NMR (400 MHz, CDCl3) δ(ppm); 1.26(s, 6H), 1.29(s, 6H), 1.70(s, 4H), 3.50(s, 3H), 5.18(s, 2H), 6.87(dd, J=8.4, 2.4 Hz, 1H), 6.97(d, J=2.4 Hz, 1H), 7.23(d, J=8.4 Hz, 1H)

Source