Dimethyl Sulfate → (Methoxymethyl)cyclododecane

HRID 2198797

Reaction equation

HRID 2198797 reaction equation
[NH2-].[Na+].[OH:3][CH2:4][CH:5]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.S(OC)(O[CH3:21])(=O)=O.[OH-].[Na+]>C1(C)C(C)=CC=CC=1>[CH:5]1([CH2:4][O:3][CH3:21])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 24533Sodium amideHCID 74686Cyclododecanemethanol

Product 1

HCID 3018712(Methoxymethyl)cyclododecane

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

25 g (0.65 mol) of sodium amide was introduced into 150 ml of xylene and heated to boiling under agitation. Within one hour, 99 g (0.5 mol) of hydroxymethylcyclododecane, dissolved in 750 ml of xylene, was added dropwise to the boiling suspension. To complete the alcoholate formation the mixture was heated for another two hours under reflux. Thereafter 44 g (0.35 mol) of dimethyl sulfate was added dropwise. The reaction mixture was heated under reflux for another four hours and then poured into a mixture of ice and 35 g of sodium hydroxide. The organic phase was washed with water, dried with Na2SO4, and then distilled.

Workup

  1. temperatureheated
  2. additionwas added dropwise to the boiling suspension
  3. temperaturewas heated for another two hours
  4. temperatureunder reflux
  5. temperatureThe reaction mixture was heated
  6. temperatureunder reflux for another four hours
  7. washThe organic phase was washed with water
  8. dry with materialdried with Na2SO4
  9. distillationdistilled

Sources & evidence

ORD record
ord-cb053392c31642de9e05f9ccbe32356c
Source dataset
uspto-grants-1982_11
Patent number
US04359588

Linked notes

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