Water → 2-Hydroxymethyl-2-n-propyl propan-1,3-diol trimethanesulphonate

HRID 1494666

Reaction equation

HRID 1494666 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][C:8]([CH2:13][CH2:14][CH3:15])([CH2:11][OH:12])[CH2:9][OH:10].[OH2:16]>N1C=CC=CC=1.C(OCC)C>[CH3:1][S:2]([OH:4])(=[O:6])=[O:3].[CH3:1][S:2]([OH:4])(=[O:16])=[O:3].[CH3:1][S:2]([OH:4])(=[O:6])=[O:3].[OH:6][CH2:7][C:8]([CH2:13][CH2:14][CH3:15])([CH2:11][OH:12])[CH2:9][OH:10]

Participants

6

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81928Butylidynetrimethanol

Product 1

HCID 867448822-Hydroxymethyl-2-n-propyl propan-1,3-diol trimethanesulphonate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

Methanesulphonyl chloride (74.0 g) was added dropwise over 30 minutes to a solution of 2-hydroxymethyl-2-n-propylpropan-1,3-diol 2× 2× 2-hydroxymethyl-2-n-propyl g) (m.pt. (28.0 g) in dry pyridine (200 ml) under nitrogen at 0° C. The mixture was allowed to warm to room temperature. After stirring for 18 hours the mixture was poured into water (200 ml) and extracted with chloroform (2 × 200 ml). The chloroform extracts were washed with water (2 × 100 ml), dried over anhydrous magnesium sulphate and evaporated in vacuo to give a brown solid. This was stirred in dry diethyl ether (200 ml) to give 2-hydroxymethyl-2-n-propyl propan-1,3-diol trimethanesulphonate as a white solid. (70.0 g)(m.pt.103.6°).

Workup

  1. customat 0° C
  2. extractionextracted with chloroform (2 × 200 ml)
  3. washThe chloroform extracts were washed with water (2 × 100 ml)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated in vacuo
  6. customto give a brown solid

Sources & evidence

ORD record
ord-dc9e61598595455192694dfc747116e7
Source dataset
uspto-grants-1991_06
Patent number
US05026874

Linked notes

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