1-Propanol → 1-Chloro-3-propoxy-2-propanol

HRID 259976Notes

Reaction equation

HRID 259976 reaction equation
[CH2:1]([OH:4])[CH2:2][CH3:3].[CH2:5]([CH:7]1[O:9][CH2:8]1)[Cl:6]>>[Cl:6][CH2:5][CH:7]([OH:9])[CH2:8][O:4][CH2:1][CH2:2][CH3:3]

Participants

3

Reactant 2

HCID 10311-PropanolHCID 7835Epichlorohydrin

Product 1

HCID 2435531-Chloro-3-propoxy-2-propanolYield 74%

Procedure

A mixture of 300 g 1-propanol (5.0 mol), 231 g epichlorohydrin and 10 g ion exchange resin was refluxed for 22 hours. The reaction mixture was then cooled, filtered and distilled to give 281 g of 1-chloro-3propoxy-2-propanol (74% yield). Reaction of this product with paraformaldehyde (2.8 mol) gave 202 g of product (69% yield) having the following structure: ##STR23##

Workup

  1. temperaturewas refluxed for 22 hours
  2. temperatureThe reaction mixture was then cooled
  3. filtrationfiltered
  4. distillationdistilled

Sources & evidence

ORD record
ord-d8e492b47d4d4f949f35a15692481e36
Source dataset
uspto-grants-1996_06
Patent number
US05523496

Reaction notes

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