HCID 54130317, compound → HCID 54481740, compound

HRID 359615Notes

Reaction equation

HRID 359615 reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][C:7]([CH:8]=[C:9]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[C:17]([CH3:22])([CH3:21])[CH2:16][CH2:15][C:14]3([CH3:24])[CH3:23])[CH3:10])=[CH:6][CH:5]=1)([O-])=O>C(O)(=O)C.O.[Fe]>[CH3:21][C:17]1([CH3:22])[CH2:16][CH2:15][C:14]([CH3:23])([CH3:24])[C:13]2[CH:12]=[C:11]([C:9]([CH3:10])=[CH:8][C:7]3[CH:25]=[CH:26][C:4]([NH2:1])=[CH:5][CH:6]=3)[CH:20]=[CH:19][C:18]1=2

Participants

5

Reactant 1

HCID 54130317HCID 54130317, compound

Product 1

HCID 54481740HCID 54481740, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent3×

Procedure

6 g of 6-[p-nitro-α-methylstyryl]-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene are dissolved in 200 ml of acetic acid and, after heating to 90°, treated within 2 minutes with 4.5 g of activated iron powder. Thereafter, 60 ml of water are added thereto and, after a further 30 minutes, the mixture is again treated with 60 ml of water. After stirring at 90° for 1 hour the reaction mixture is cooled, diluted with water and extracted with ether. The organic phase is washed with water, dilute soda solution and again with water. After drying with sodium sulphate the organic phase is evaporated and there is obtained a brown oil which is purified by filtration over silica gel (elution agent hexane/acetic acid 4:1). Recrystallization from hexane gives 4.5 g of p-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]aniline in colourless crystals, melting point 106°-108°.

Workup

  1. temperatureafter heating to 90°
  2. temperatureis cooled
  3. extractionextracted with ether
  4. washThe organic phase is washed with water
  5. additiondilute soda solution
  6. dry with materialAfter drying with sodium sulphate the organic phase
  7. customis evaporated
  8. customthere is obtained a brown oil which
  9. filtrationis purified by filtration over silica gel (elution agent hexane/acetic acid 4:1)
  10. customRecrystallization from hexane

Sources & evidence

ORD record
ord-6fbcae9abd974b138da94c2455825d81
Source dataset
uspto-grants-1991_03
Patent number
US05001276

Reaction notes

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