Hydrochloric Acid → HCID 73472652, compound

Participants

Reaction Conditions

Reaction Steps

3-Methyl-2-buten-1-ol (8.6 g, 100 mmol) was mixed with isoamyl nitrite (28 g, 240 mmol) at room temperature. The solution was cooled to -5° C. in an ice-salt bath and concentrated HCl (11 mL, 100 mmol) was added dropwise. The reaction temperature was maintained between -5° to 0° C. during the addition. The reaction mixture was stirred in the ice-salt bath for 60 min, filtered and washed with cooled ether to give a white solid. Yield 4.5 g (30%). top: 114°-115° C. MS (m/z): 305 (2M+2+H)+, 303 (2M+H)+, 154(M+2+H)+, 152 (M+H)+. 1H NMR (DMSO-d6): ε 1.56 (d) and 1.80 (s) [6H, (CH3)2CCHNO and (CH3)2CC=NOH)], 4.10 (m) and 4.26 (s) [2H, HOCH2CH(NO) and HOCH2C=NOH], 5.2 (b, 1H, HOCH2), 5.93 (t) and 11.28 (b) [1H, CHN=O and C=NOH]. 13C (DMSO-d6) ε 29.9 [(CH3)2CCHNO], 31.5 [(CH3)2CC=NOH], 53.7 [(CH3)2CCHNO], 59.7 [(CH3 )2CC=NOH], 69.4 [HOCH2CH (NO)], 74.1 [HOCH2C=NOH], 160.2 [CHN=O and C=NOH]. Anal. Calcd. for C5H10NC10: C, 39.62; H, 6.65; N, 9.24; Cl, 23.39; O, 21.11. Found: C, 39.73; H, 6.87; N, 9.15; Cl, 23.43.

Provenance & Evidence