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

HRID 263221Notes

Reaction equation

HRID 263221 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 47%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Concentrated hydrochloric acid (28.4 ml) was added dropwise over 1 hour to a mixture of 1-(p-chloro)phenoxy-3-methylbut-2-ene (VI; R=CH2OC6H4.Cl, R1 =R2 =CH3) (56.1 g) and amyl nitrite (42.6 ml) in glacial acetic acid (56.7 ml) at -5° to 0° (ice-salt bath). After a further 1 hour at -5° to 0°, the mixture was filtered. The solid so obtained was washed with benzene and recrystallised from benzene after drying to give the nitrosochloride (V) (35.31 g, yield 47%) as pale yellow crystals, m.p. 124°-5° (decomp.).

Workup

  1. filtrationthe mixture was filtered
  2. customThe solid so obtained
  3. washwas washed with benzene
  4. customrecrystallised from benzene
  5. customafter drying

Sources & evidence

ORD record
ord-6b2dbb523b534c8a91e1898d508c3e43
Source dataset
uspto-grants-1979_05
Patent number
US04156725

Reaction notes

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