p-Toluenesulfonic acid → Cyclohexanone, 4-[(tetrahydro-2H-pyran-2-yl)oxy]-

HRID 1657562Notes

Reaction equation

HRID 1657562 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.[O:9]1[CH:14]=[CH:13][CH2:12][CH2:11][CH2:10]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC>[O:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[O:8][CH:5]1[CH2:6][CH2:7][C:2](=[O:1])[CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 5437064-Hydroxycyclohexanone

Product 1

HCID 10012971Cyclohexanone, 4-[(tetrahydro-2H-pyran-2-yl)oxy]-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution comprising 10 g. of 4-hydroxycyclohexanone, 10 g. of dihydropyran and 0.5 g. of p-toluenesulfonic acid in 100 ml. of ether is allowed to stand at room temperature for about 2.5 hours. The solution is then washed with saturated aqueous sodium bicarbonate solution and brine, 50 ml. of dry benzene added and the solution then evaporated to dryness to give 4-[(tetrahydropyran-2-yl)oxy]cyclohexanone as an oil.

Workup

  1. washThe solution is then washed with saturated aqueous sodium bicarbonate solution and brine, 50 ml
  2. additionof dry benzene added
  3. customthe solution then evaporated to dryness

Sources & evidence

ORD record
ord-03f6c97d89e84219b6c210a65545ae43
Source dataset
uspto-grants-1976_06
Patent number
US03960961

Reaction notes

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