2,6-Dimethylphenol → Phenol, 2,6-dimethyl-4-nitroso-

HRID 1980562Notes

Reaction equation

HRID 1980562 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].[N:10]([O-])=[O:11].[Na+]>C(O)(=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([N:10]=[O:11])[CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9]

Participants

4

Reactant 2

HCID 113352,6-DimethylphenolHCID 23668193Sodium Nitrite

Product 1

HCID 83351Phenol, 2,6-dimethyl-4-nitroso-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

25 Grams of 2,6-dimethylphenol was dissolved in 246 ml of 50% aqueous glacial acetic acid solution. To this solution being kept at 15° C. or lower was added dropwise 91 g of 30% aqueous sodium nitrite solution, whereby 2,6-dimethyl-p-nitrosophenol was obtained. The compound was reduced to be converted to an amino compound. The amino compound was subjected to diazotization at 0° to 2° C. Into the resulting reaction mixture was poured a 50% aqueous zinc chloride solution. By thorough mixing, a double salt of a diazonium salt with zinc chloride was deposited. Infrared absorption spectra (KBr tablet method): around 3300 cm-1, 2200 cm-1, 1570 cm-1, 1080 cm-1, 930 cm-1 ; ultraviolet absorption spectra (solvent: water), wavelength at maximum absorption: 364 nm. SYNTHESIS EXAMPLES 5 AND 6

Workup

  1. custombeing kept at 15° C.

Sources & evidence

ORD record
ord-143e580dd7a347fdb2be88017a3b8a1b
Source dataset
uspto-grants-1985_04
Patent number
US04510226

Reaction notes

Loading…