2,2,4-Trimethyl-1,3-pentanediol → HCID 20442445, compound

HRID 1632792Notes

Reaction equation

HRID 1632792 reaction equation
[CH3:1][C:2]([CH3:10])([CH:5]([OH:9])[CH:6]([CH3:8])[CH3:7])[CH2:3][OH:4].[C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21](Cl)(=[O:23])=[O:22])([O:13][CH3:14])=[O:12]>N1C=CC=CC=1>[C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([O:4][CH2:3][C:2]([CH3:10])([CH3:1])[CH:5]([O:9][S:21]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:11]([O:13][CH3:14])=[O:12])(=[O:23])=[O:22])[CH:6]([CH3:8])[CH3:7])(=[O:23])=[O:22])([O:13][CH3:14])=[O:12]

Participants

4

Reactant 2

HCID 89462,2,4-Trimethyl-1,3-pentanediolHCID 117830Benzoic acid, 2-(chlorosulfonyl)-, methyl ester

Product 1

HCID 20442445HCID 20442445, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Into a one-liter, four-necked, round bottom flask equipped with stirrer, condenser, thermometer and addition funnel, 36.5 parts of 2,2,4-trimethyl-1,3-pentanediol and 632.0 parts of pyridine were mixed under a nitrogen blanket and cooled to 0° C. using an ice water bath. Subsequently, 117.3 parts of o-carbomethoxybenzenesulfonyl chloride were added in small portions over a two hour period while maintaining the temperature below 10° C. The aforesaid mixture was maintained at a temperature between 0° C. and 10° C. for a two hour period and then refrigerated at 15° C. for at least twenty-four hours prior to work-up. For work-up the reaction mixture was poured into 1000 parts of ice water and subsequently extracted with 500 parts of methylene chloride. The organic layer was washed successively with cold, dilute 6N sulfuric acid (twice with 500 part-portions), cold, dilute sodium bicarbonate (once with 500 parts), and water (until the water layer was neutral to pH paper). It was then dried over sodium sulfate, filtered, and the solvent removed in vacuo to yield the 2,2,4-trimethyl-1,3-pentanediyl bis-(ortho-carbomethoxybenzenesulfonate).

Workup

  1. customInto a one-liter, four-necked, round bottom flask equipped with stirrer, condenser
  2. additionthermometer and addition funnel
  3. temperaturewhile maintaining the temperature below 10° C
  4. temperatureThe aforesaid mixture was maintained at a temperature between 0° C. and 10° C. for a two hour period
  5. waitrefrigerated at 15° C. for at least twenty-four hours
  6. extractionsubsequently extracted with 500 parts of methylene chloride
  7. washThe organic layer was washed successively with cold,
  8. additiondilute 6N sulfuric acid (twice with 500 part-portions), cold, dilute sodium bicarbonate (once with 500 parts), and water (until the water layer
  9. dry with materialIt was then dried over sodium sulfate
  10. filtrationfiltered
  11. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-11774623b9b042a397eb4472c293aa75
Source dataset
uspto-grants-1984_10
Patent number
US04477618

Reaction notes

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