Hydrochloric Acid → (3-Chloro-3-methyl-2-nitrosobutoxy)benzene

HRID 263220Notes

Reaction equation

HRID 263220 reaction equation
[ClH:1].[O:2]([CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N:14]([O:16]CCCCC)=O>C(O)(=O)C>[Cl:1][C:11]([CH3:13])([CH:10]([N:14]=[O:16])[CH2:9][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10026Pentyl nitriteHCID 564931Benzene, ((3-methyl-2-butenyl)oxy)-

Product 1

HCID 21316467(3-Chloro-3-methyl-2-nitrosobutoxy)benzeneYield 50%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Concentrated hydrochloric acid (7.8 ml) was added dropwise over 1 hour to a mixture of 1-(p-methoxy)phenoxy-3-methylbut-2-ene (VI; R=CH2OC6H4.OCH3, R1 =R2 =CH3) (12.0 g) and amyl nitrite (11.7 ml) in glacial acetic acid (15.6 ml) at 0° C. (ice-salt bath). A white precipitate separated and this was filtered off and dried to give the nitrosochloride (V) (8.0 g, yield 50%) as colourless crystals, m.p. 137°.

Workup

  1. customA white precipitate separated
  2. filtrationthis was filtered off
  3. customdried

Sources & evidence

ORD record
ord-bd778db085344263b8d88126bd64e6ce
Source dataset
uspto-grants-1979_05
Patent number
US04156725

Reaction notes

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