Nitric Acid → 1,1,4,4-Tetramethyl-6-nitro-1,2,3,4-tetrahydronaphthalene

HRID 1599112Notes

Reaction equation

HRID 1599112 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1([CH3:18])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH3:17])([CH3:16])[CH2:8][CH2:7]1.O>C(O)(=O)C.C(OC(=O)C)(=O)C>[N+:1]([C:13]1[CH:12]=[CH:11][C:10]2[C:9]([CH3:17])([CH3:16])[CH2:8][CH2:7][C:6]([CH3:18])([CH3:5])[C:15]=2[CH:14]=1)([O-:4])=[O:2]

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 811861,1,4,4-Tetramethyltetralin

Product 1

HCID 139871261,1,4,4-Tetramethyl-6-nitro-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 7918Acetic AnhydrideSolvent

Procedure

77.2 ml of glacial acetic acid and 20.8 ml of nitric acid (98% strength) were mixed while cooling and then added dropwise within 2 hours to a solution of 65.8 g (0.35 mol) of 1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene in 154 ml of glacial acetic acid and 257 ml of acetic anhydride in a salt/ice bath. After the addition was complete, the reaction mixture was warmed to room temperature and stirred overnight. The solution was then poured into water, and the precipitate was filtered off with suction, washed with water and dried. 79.7 g of crude 2-nitro-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene of melting point 46°-50° C. were obtained.

Workup

  1. temperaturewhile cooling
  2. additionAfter the addition
  3. filtrationthe precipitate was filtered off with suction
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-75c85c564bf444c08ccd1db865f7a165
Source dataset
uspto-grants-1998_04
Patent number
US05739374

Reaction notes

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