Ethyl vinyl ether → 3-Chloro-2-(1-ethoxyethoxy)propyl acetate

HRID 1075311Notes

Reaction equation

HRID 1075311 reaction equation
[C:1]([O:4][CH2:5][CH:6]([OH:9])[CH2:7][Cl:8])(=[O:3])[CH3:2].[CH:10]([O:12][CH2:13][CH3:14])=[CH2:11].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[C:1]([O:4][CH2:5][CH:6]([O:9][CH:10]([O:12][CH2:13][CH3:14])[CH3:11])[CH2:7][Cl:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8023Ethyl vinyl etherHCID 980693-Chloro-2-hydroxypropyl acetateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 131539053-Chloro-2-(1-ethoxyethoxy)propyl acetateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 30.5 g (0.20 mol) of 3-chloro-2-hydroxy-1-propyl acetate (prepared in Example 1), 22 g (0.30 mol) of ethyl vinyl ether, and 7.5 g (0.030 mol) of pyridinium p-toluenesulfonate in 150 mL of methylene chloride was stirred at room temperature for 6 hours. The solution was then washed with 75 mL of water, dried and stripped of solvent in vacuo to give 44.0 g (98.0%) of 3-chloro-2-(1-ethoxyethoxy)-1-propyl acetate: 1H NMR (CDCl3) δ1.05-1.37 (overlapping t and d, 6H, --CH2CH3 and --CHCH3); 2.07 (s, 3H, --COCH); 3.53 and 4.12 (m. 7H, --CH2CHCH2 and --CH2CH3); 4.72 (q, J=4 Hz, 1H, --CHCH3); IR (film) 1740 cm-1 (--COCH3 ). The unpurified product was used in the next step.

Workup

  1. washThe solution was then washed with 75 mL of water
  2. customdried

Sources & evidence

ORD record
ord-8927f2b97820461aaf0453cd3e4bdda9
Source dataset
uspto-grants-1983_07
Patent number
US04395561

Reaction notes

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