Acetic Acid → HCID 22596836, compound

HRID 1760827Notes

Reaction equation

HRID 1760827 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2.C(O)(=O)C.[N+:19]([O-])([OH:21])=[O:20]>C(OC(=O)C)(=O)C>[N+:19]([CH:10]1[CH2:11][C:2]([CH3:14])([CH3:1])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=2[C:9]1([CH3:13])[CH3:12])([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 811861,1,4,4-Tetramethyltetralin

Product 1

HCID 22596836HCID 22596836, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene (20.0 g, 106.2 mmole) in 85 ml of acetic anhydride at 0° C. was treated with 12.2 mL of acetic acid followed by 11.1 mL of nitric acid (70%) and was allowed to warm to room temperature. After 24 hours the reaction mixture was poured onto 300 mL of ice-water and extracted with three 150 mL portions of ether. The combined organic extracts were washed with four 100 mL portions of 15% aqueous sodium hydroxide solution, two 200 mL portions of water and one 200 mL portion of saturated aqueous sodium chloride solution. The organic phase was dried, filtered and concentrated in vacuo to provide 23.93 g (97%) of 6-nitro-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene (3) as a pale yellow solid.

Workup

  1. extractionextracted with three 150 mL portions of ether
  2. washThe combined organic extracts were washed with four 100 mL portions of 15% aqueous sodium hydroxide solution, two 200 mL portions of water and one 200 mL portion of saturated aqueous sodium chloride solution
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c9b202d8e94947d08174951649a5f4c5
Source dataset
uspto-grants-2005_01
Patent number
US06844466B2

Reaction notes

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