Nitric Acid → 2-(Hydroxymethyl)-4-methyl-6-nitrophenol

HRID 1602045Notes

Reaction equation

HRID 1602045 reaction equation
C([C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]([OH:10])[C:4]=1[CH2:11][OH:12])O.[N+:13]([O-])([OH:15])=[O:14]>O>[N+:13]([C:6]1[CH:7]=[C:8]([CH3:9])[CH:3]=[C:4]([CH2:11][OH:12])[C:5]=1[OH:10])([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 21641889HCID 21641889, compound2×

Product 1

HCID 132195342-(Hydroxymethyl)-4-methyl-6-nitrophenolYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The 6-nitro-2-methylol p-cresol was prepared by charging 134.3 grams of bis-methylol para cresol (BMPC) (assay: 97.9%, melting point: 124.5 to 126.5° C.), and 3000 grams of deionized water into a 5 liter, wide mouth beaker and stirring to achieve a colloidal suspension of the BMPC before 200 grams of concentrated nitric acid was added in 30 minutes as the temperature was maintained between 20 and 30° C. The mixture was mixed an additional 24 hours at room temperature before a Buchner funnel filtration. The wetcake was washed with deionized water until the effluent achieved a pH of 6. The wetcake was then vacuum oven dried (30-35° C.,<10 torr) until the residual water assay was less than 1 percent. Yield: 80 to 85%.

Workup

  1. additionwas added in 30 minutes as the temperature
  2. temperaturewas maintained between 20 and 30° C
  3. additionThe mixture was mixed an additional 24 hours at room temperature before a Buchner funnel filtration
  4. washThe wetcake was washed with deionized water until the effluent
  5. dry with materialvacuum oven dried (30-35° C.,<10 torr) until the residual water assay

Sources & evidence

ORD record
ord-2b185c4caec94e88972d1c4346207320
Source dataset
uspto-grants-1999_11
Patent number
US05981135

Reaction notes

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