Reaction #75441

Reaction equation

HCl

isoamyl nitrite

1-ethoxy-3-methyl-2-butene

→

title product

3-Chloro-3-methyl-1-ethoxy-2-nitrosobutane

Conditions

Workup

1. 1
   workup.ADDITIONduring the addition
2. 2
   FiltrationThe product was filtered
3. 3
   Washwashed with a cold (−20° C.) 1:1 mixture of ethanol and ether
4. 4
   WashThe solid was further washed with ether

Procedure

Concentrated HCl was added to a cooled (0-5° C.) solution of isoamyl nitrite (14.0 g, 0.12 mol) and 1-ethoxy-3-methyl-2-butene (6.84 g, 0.06 mol). The temperature was maintained below, 5° C. during the addition and the reaction mixture was stirred at 5° C. for an additional 30 min. The product was filtered and washed with a cold (−20° C.) 1:1 mixture of ethanol and ether. The solid was further washed with ether to afford the title product as a white solid. Yield 6.9 g (64%). mp: 84-85° C. 1H NMR (CDCl3) δ1.12 (t, 3H, CH2CH3), 1.65 (d, 6H, CH3), 3.49 and 3.95 (m, 2H, CH2OCH2CH3), 4.15 (m, 2H,CH2CH3), 6.12 (dd, 1H, [CH3)2C═CH—]. MS: 180 (M+H)+.

Source