Thionyl Chloride → 1003-85-6

HRID 237463Notes

Reaction equation

HRID 237463 reaction equation
[S:1](Cl)(Cl)=[O:2].[CH3:5][C:6]([CH3:11])([CH2:9][OH:10])[CH2:7][OH:8]>ClCCl>[CH3:5][C:6]1([CH3:11])[CH2:9][O:10][S:1](=[O:2])[O:8][CH2:7]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 31344Neopentyl glycol

Product 1

HCID 108772941003-85-6

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

Thionylchloride (735 mL) is added to a solution of 2,2-dimethylpropane-1,3-diol (1 g) in dichloromethane (10 mL) chilled in an ice bath. The mixture is heated to 40° C. for 3 hours and partitioned between saturated aqueous NaHCO3 solution and dichloromethane. The organic phase is washed with brine, dried (MgSO4) and concentrated to give the title compound. Yield: 535 mg; TLC: rf=0.65 (silicagel, cyclohexane/ethyl acetate 3:1).

Workup

  1. temperaturechilled in an ice bath
  2. custompartitioned between saturated aqueous NaHCO3 solution and dichloromethane
  3. washThe organic phase is washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-af424466045b46e7854c08638e34faf0
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

Loading…