Hydrochloric Acid → 1-Ethoxy-3-chloro-3-methyl-2-nitrosobutane
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]>>[CH2:10]([O:12][CH2:13][CH:14]([N:2]=[O:4])[C:15]([Cl:1])([CH3:17])[CH3:16])[CH3:11]Participants
4
Conditions
- Temperature
- 5 °C
Procedure
Concentrated HCl was added to a cooled (0°-5° C.) solution of isoamyl nitrite (14.0 g, 120 mmol) and 1-ethoxy-3-methyl-2-butene (6.84 g, 60 mmol). 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 a white solid. Yield: 6.9 g (64%); mp 84°-85° C. 1H NMR (CDCl3) ε 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: (M+H)+ =180.
Workup
- temperatureThe temperature was maintained below 5° C. during the addition
- filtrationThe product was filtered
- washwashed with a cold (-20° C.) 1:1 mixture of ethanol and ether
- washThe solid was further washed with ether
- customto afford a white solid
Sources & evidence
- ORD record
- ord-1d59a73a1f1348fa8ffd0f121ec538b6
- Source dataset
- uspto-grants-1997_05
- Patent number
- US05627286
Reaction notes
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