2,3-Butanediol → HCID 57720059, compound

HRID 1985592Notes

Reaction equation

HRID 1985592 reaction equation
[CH3:1][CH:2]([OH:6])[CH:3]([OH:5])[CH3:4].[C:7]1([CH3:17])[CH:12]=[CH:11][C:10](S(O)(=O)=O)=[CH:9][CH:8]=1.[C:18]1(C)C=CC=CC=1>>[CH3:4][CH:3]1[CH:2]([CH3:1])[O:6][C:8]2([CH:9]([CH3:18])[CH2:10][CH2:11][CH2:12][CH:7]2[CH3:17])[O:5]1

Participants

4

Reactant 3

HCID 2622,3-ButanediolHCID 1140TolueneHCID 6101p-Toluenesulfonic acid

Product 1

HCID 57720059HCID 57720059, compound

Conditions

Temperature
120 °C

Procedure

A reaction flask equipped with a Dean Stark trap was charged with 2,6-dimethyl cyclohehanone (200 g), 2,3-butanediol (315 g), p-toluenesulfonic acid (2 g) and toluene (300 mL). The reaction mass was heated to reflux (110-130° C.). Water (36 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 2,3,6,10-tetramethyl-1,4-dioxaspiro[4,5]decane (265 g)), which had a boiling point of 104° C. at a pressure of 16 mmHg.

Workup

  1. customA reaction flask equipped with a Dean Stark trap
  2. temperatureThe reaction mass was heated
  3. customWater (36 mL) was collected in the Dean Stark trap
  4. customWhen no water was recovered the reaction mass
  5. temperaturewas cooled to an ambient temperature
  6. washwashed with brine
  7. customPurification
  8. distillationby vacuum distillation

Sources & evidence

ORD record
ord-1df32608bbf54058ade937eac99e49ac
Source dataset
uspto-grants-2009_06
Patent number
US07547668B1

Reaction notes

Loading…