Hydrochloric Acid → Phenol, 2,6-bis(1,1-dimethylethyl)-4-nitroso-

HRID 2165808Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].C1(O)C=CC=CC=1.Cl.[N:24]([O-])=[O:25].[Na+]>O.C(O)C>[C:11]([C:7]1[CH:8]=[C:9]([N:24]=[O:25])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:15])([CH3:14])([CH3:13])[CH3:12]

Participants

Conditions

Temperature: 0 °C

Procedure

In a 500 ml round flask equipped with a thermometer, stirrer and nitrogen inlet was added 2,6-ditertbutylphenol (50 g, 0.243 moles) and ethanol (95%, I00 ml). The solution was stirred until all of the phenol dissolved. The solution was then cooled to 0° C and concentrated hydrochloric acid (26.3 g, 0.267 moles) was slowly added. A solution of sodium nitrite (17.56 g, 0.254 moles) in water (75 ml) was then added dropwise so as to keep the temperature of the reaction between 0 °and 10° C. (1 hr). The solution became quite thick and more ethanol was added accordingly, for efficient stirring. After the addition was completed, the reaction mixture was stirred for 1 hr and it was then poured into a beaker of ice water (~5 L). The yellow green precipitate was filtered off washed, with water and air dried. The yield was 98 wt%. (210-213° C.).

Workup

customIn a 500 ml round flask equipped with a thermometer, stirrer and nitrogen inlet
dissolutiondissolved
customthe temperature of the reaction between 0 °and 10° C. (1 hr)
additionAfter the addition
filtrationThe yellow green precipitate was filtered off
washwashed, with water and air
customdried
custom(210-213° C.)

Sources & evidence

ORD record: ord-fabeff54d7944ac8bc351541e993e465
Source dataset: uspto-grants-1990_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04941985

Reaction notes

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