Hydrochloric Acid → Chloromethyl 1,3-Diacetoxy-2-propyl Ether

HRID 330587

Reaction equation

HRID 330587 reaction equation
[C:1]([O:4][CH2:5][CH:6]([O:12][CH2:13]OC(=O)C)[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2].[ClH:18]>C(Cl)Cl>[C:1]([O:4][CH2:5][CH:6]([O:12][CH2:13][Cl:18])[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 97948881,3-Propanediol, 2-((acetyloxy)methoxy)-, 1,3-diacetate

Product 1

HCID 19868843Chloromethyl 1,3-Diacetoxy-2-propyl Ether

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.33 g (9.4 mmoles) of acetoxymethyl 1,3-diacetoxy-2-propyl ether in 22 ml of sieve-dried methylene chloride was stirred at room temperature while a slow stream of anhydrous hydrogen chloride was passed through the solution. Anhydrous conditions were maintained throughout the reaction. After two hours the reaction was judged to be complete by nuclear magnetic resonance spectroscopy. The reaction mixture was purged with nitrogen and concentrated in vacuo. The residue was taken up in a small volume of toluene and concentrated in vacuo. This was repeated twice and then the residue was pumped in vacuo to remove residual solvent. The yield of chloromethyl 1,3-diacetoxy-2-propyl ether is 1.92 g (91%).

Workup

  1. temperatureAnhydrous conditions were maintained throughout the reaction
  2. customThe reaction mixture was purged with nitrogen
  3. concentrationconcentrated in vacuo
  4. concentrationconcentrated in vacuo
  5. customto remove residual solvent

Sources & evidence

ORD record
ord-04ea1fadc7c44301bd4af014ed4bcf8c
Source dataset
uspto-grants-1990_01
Patent number
US04897479

Linked notes

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