Ethylene Glycol → HCID 13778953, compound

HRID 1985589Notes

Reaction equation

HRID 1985589 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[C:5]1([CH3:15])[CH:10]=[CH:9][C:8](S(O)(=O)=O)=[CH:7][CH:6]=1.[C:16]1(C)C=CC=CC=1>>[CH3:15][CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([CH3:16])[C:6]21[O:4][CH2:1][CH2:2][O:3]2

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 1140TolueneHCID 6101p-Toluenesulfonic acid

Product 1

HCID 13778953HCID 13778953, compound

Conditions

Temperature
120 °C

Procedure

A reaction flask equipped with a Dean Stark trap was charged with 2,6-dimethyl cyclohehanone (190 g), ethylene glycol (155 g), p-toluenesulfonic acid (2 g) and toluene (200 mL). The reaction mass was heated to reflux (110-130° C.). Water (27 mL) was collected in the Dean Stark trap. When no water was recovered, the reaction mass was cooled to an ambient temperature, neutralized with 10% aqueous sodium carbonate (100 mL) and washed with brine. Purification by vacuum distillation afforded 6,10-dimethyl-1,4-dioxaspiro[4,5]decane (225 g), which had a boiling point of 93° C. at a pressure of 22 mmHg.

Workup

  1. customA reaction flask equipped with a Dean Stark trap
  2. temperatureThe reaction mass was heated
  3. customWater (27 mL) was collected in the Dean Stark trap
  4. customWhen no water was recovered
  5. temperaturethe reaction mass was cooled to an ambient temperature
  6. washwashed with brine
  7. customPurification
  8. distillationby vacuum distillation

Sources & evidence

ORD record
ord-6567baefffb44eb58088bc0e7d7bc0d2
Source dataset
uspto-grants-2009_06
Patent number
US07547667B1

Reaction notes

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