Water → 2-Methylpropane-1,3-diyl bis(4-methylbenzenesulfonate)

HRID 20049

Reaction equation

HRID 20049 reaction equation
[CH3:1][CH:2]([CH2:5][OH:6])[CH2:3][OH:4].[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1.[OH2:18]>N1C=CC=CC=1>[S:13]([O:4][CH2:3][CH:2]([CH3:1])[CH2:5][O:6][S:13]([C:10]1[CH:11]=[CH:12][C:7]([CH3:17])=[CH:8][CH:9]=1)(=[O:14])=[O:18])([C:10]1[CH:11]=[CH:12][C:7]([CH3:17])=[CH:8][CH:9]=1)(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 75103Methylpropanediol

Product 1

HCID 126504682-Methylpropane-1,3-diyl bis(4-methylbenzenesulfonate)

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Methylpropane-1,3-diol (50 g, 555 mmol) was dissolved in 555 ml pyridine and cooled to 0° C. p-Toluenesulfonyl chloride (212 g, 1110 mmol) was added and stirring was continued over night. 200 ml H2O was added and the reaction was extracted with DCM (2×1L). The combined organic extracts were dried over MgSO4 and evaporated. The product was recrystallized from EtOH/Hex and the product was obtained as a white solid. MS m/z: 399.0 (M+1).

Workup

  1. additionwas added
  2. waitwas continued over night
  3. extractionthe reaction was extracted with DCM (2×1L)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. customevaporated
  6. customThe product was recrystallized from EtOH/Hex
  7. customthe product was obtained as a white solid

Sources & evidence

ORD record
ord-7d87b2b100184cfc8cc1e9b3684f503c
Source dataset
uspto-grants-2010_06
Patent number
US07745484B2

Linked notes

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