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

HRID 263223Notes

Reaction equation

HRID 263223 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 42%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Concentrated hydrochloric acid (7.8 ml) was added dropwise over 1.5 hour to a mixture of 1-(p-methyl)phenoxy-3-methylbut-2-ene (VI; R=CH2OC6H4.CH3, R1 =R2 =CH3) (12.85 g) and amyl nitrite (11.7 ml) in glacial acetic acid (15.6 ml) at -5° to 0° (ice-salt bath). After a further 1 hour at -5° to 0°, the mixture was filtered. The yellow solid so obtained was washed with acetone and recrystallised from acetone to give the nitrosochloride (V) (7.5 g, yield 42%) as white crystals, m.p. 144°-5° (decomp.).

Workup

  1. filtrationthe mixture was filtered
  2. customThe yellow solid so obtained
  3. washwas washed with acetone
  4. customrecrystallised from acetone

Sources & evidence

ORD record
ord-daf7f12f4ca645d096651fd604faf2dd
Source dataset
uspto-grants-1979_05
Patent number
US04156725

Reaction notes

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