p-Toluenesulfonic acid → 3-Methoxymethyl2,4-dioxaspiro[5.5]undecane

HRID 359948Notes

Reaction equation

HRID 359948 reaction equation
[CH2:1]([C:3]1([CH2:9][OH:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)[OH:2].[CH3:11][O:12][CH2:13][CH:14]=O.C1CCCCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH3:11][O:12][CH2:13][CH:14]1[O:10][CH2:9][C:3]2([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]2)[CH2:1][O:2]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8078CyclohexaneHCID 91563MethoxyacetaldehydeHCID 250594Cyclohexanedimethanol

Product 1

HCID 145979503-Methoxymethyl2,4-dioxaspiro[5.5]undecaneYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 288 g (2 moles) of 1,1-dimethylolcyclohexane, 191 g (2.2 moles) of 85% strength methoxyacetaldehyde and 250 ml of cyclohexane was heated with 2 g of p-toluenesulfonic acid under a water separator until water no longer separated off. The resulting solution was washed with dilute sodium hydroxide solution, the solvent was stripped off under reduced pressure and the residue was subjected to fractional distillation under reduced pressure. 388 g (97% yield) of 3-methoxymethyl-2,4-dioxaspiro[5.5]undecane of boiling point 95° C./1 mbar were obtained.

Workup

  1. customno longer separated off
  2. washThe resulting solution was washed with dilute sodium hydroxide solution
  3. distillationthe residue was subjected to fractional distillation under reduced pressure

Sources & evidence

ORD record
ord-5755b887ebef42ce85ae06f81bb7e645
Source dataset
uspto-grants-1991_03
Patent number
US05003089

Reaction notes

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