Sulfuric Acid → 2-Chloro-2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanol

HRID 464237Notes

Reaction equation

HRID 464237 reaction equation
[CH3:1][O:2][C:3]([O:6][CH3:7])([CH3:5])[CH3:4].[Cl:8][CH:9](CO)[CH:10]([OH:13])CO.S(=O)(=O)(O)O.[OH-].[Ba+2].[OH-]>CC(C)=O.O>[Cl:8][CH:9]([CH:1]1[CH2:7][O:6][C:3]([CH3:5])([CH3:4])[O:2]1)[CH2:10][OH:13]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 64952,2-DimethoxypropaneHCID 6093286Barium hydroxideHCID 106068313-Chlorobutane-1,2,4-triol

Product 1

HCID 131868262-Chloro-2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanol

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

258 ml of 2,2-dimethoxypropane is added dropwise within 2 hours to an agitated and water-cooled solution of 272 g of 3-chloro-1,2,4-butanetriol and 0.5 ml of concen-trated sulfuric acid in one liter of acetone. The reaction is completed after another 4 hours. The solution is neutralized by adding 3.8 g of barium hydroxide. The mixture is stirred for another 30 minutes, filtered off from the solid matter, and evaporated to dryness under vacuum, producing 2-chloro-2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanol as a yellow oil.

Workup

  1. stirringThe mixture is stirred for another 30 minutes
  2. filtrationfiltered off from the solid matter
  3. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-0057310b73cc45b2b7d6571d3a9b575e
Source dataset
uspto-grants-1985_10
Patent number
US04547357

Reaction notes

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