Hydrochloric Acid → 1-Ethoxy-3-chloro-3-methyl-2-nitrosobutane

HRID 2393790Notes

Reaction equation

HRID 2393790 reaction equation
[ClH:1].[N:2]([O:4]CCC(C)C)=O.[CH2:10]([O:12][CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])[CH3:11]>>[Cl:1][C:15]([CH3:17])([CH3:16])[CH:14]([N:2]=[O:4])[CH2:13][O:12][CH2:10][CH3:11]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 54639361-Ethoxy-3-methyl-2-butene

Product 1

HCID 104197661-Ethoxy-3-chloro-3-methyl-2-nitrosobutane

Conditions

Temperature
5 °C

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) δ 1.12 (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)+.

Workup

  1. temperatureThe temperature was maintained below 5 ° C. during the addition
  2. filtrationThe product was filtered
  3. washwashed with a cold (-20° C.) 1:1 mixture of ethanol and ether
  4. washThe solid was further washed with ether

Sources & evidence

ORD record
ord-76343b08993140eca3de84216bb6dc20
Source dataset
uspto-grants-1998_09
Patent number
US05808091

Reaction notes

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