Acetic Acid → HCID 22765134, compound

HRID 2072027Notes

Reaction equation

HRID 2072027 reaction equation
[CH2:1]([C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]=1[OH:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(O)(=O)C.[N+:28]([O-])([OH:30])=[O:29]>O>[CH2:1]([C:13]1[CH:22]=[C:21]([N+:28]([O-:30])=[O:29])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]=1[OH:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 3022871Dodecyl-1-naphthol

Product 1

HCID 22765134HCID 22765134, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 50 parts of 2-n-dodecyl-1-naphthol in 500 parts of glacial acetic acid was added 28 parts of nitric acid (specific gravity 1.4). The solution was stirred at ambient temperature for 1 hour and then poured into 2,000 parts of water. The resulting mixture was extracted with 1,400 parts of ether. The ether layer was separated; washed once with water (2,000 parts), twice with 10% aqueous sodium bicarbonate solution (2,000 parts), and finally with water (2,000 parts). The ether solution was dried with anhydrous magnesium sulfate and evaporated to afford 56 parts of 2-n-dodecyl-4-nitro-1-naphthol as a viscous yellow oil, nD25 = 1.5454, which slowly crystallized to a waxy yellow solid on standing.

Workup

  1. extractionThe resulting mixture was extracted with 1,400 parts of ether
  2. customThe ether layer was separated
  3. washwashed once with water (2,000 parts), twice with 10% aqueous sodium bicarbonate solution (2,000 parts)
  4. dry with materialThe ether solution was dried with anhydrous magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-3275947517f54c1d937f4e1b15186a3f
Source dataset
uspto-grants-1977_09
Patent number
US04049705

Reaction notes

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