Reaction #6605

ord-2312dd61119e4794b7fcad57c714dd9a

Reaction equation

CC1(C)CCC(C)(C)c2cc(O)ccc21
5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthol
N#Cc1ccc(CCl)cc1
4-cyanobenzyl chloride
O=C([O-])[O-].[K+].[K+]
potassium carbonate
O
water
→
CC1(C)CCC(C)(C)c2cc(OCc3ccc(C#N)cc3)ccc21
title compound
Yield 98.6%
CC1(C)CCC(C)(C)c2cc(OCc3ccc(C#N)cc3)ccc21
4-Cyanobenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ether
Yield 98.6%

Reactants

CC1(C)CCC(C)(C)c2cc(O)ccc21
5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthol
N#Cc1ccc(CCl)cc1
4-cyanobenzyl chloride
O=C([O-])[O-].[K+].[K+]
potassium carbonate
O
water

Reagents

None

Solvents

CCC(C)=O
butanone
CN(C)C=O
dimethylformamide

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureThe mixture was cooled
  2. 2
    Filtrationthe solid was filtered off with suction
  3. 3
    Washwashed with water
  4. 4
    OtherDrying

Procedure

40.8 g (0.2 mol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthol, 30.4 g (0.2 mol) of 4-cyanobenzyl chloride and 80 g (1.2 mol) of anhydrous potassium carbonate in 400 ml of butanone and 300 ml of dimethylformamide were refluxed for 9 h. The mixture was cooled and then poured into 1.5 l of water, and the solid was filtered off with suction and washed with water. Drying resulted in 63 g of the title compound of melting point 149°-150° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05248823uspto-grants-1993_09