Ammonia → 4,8-Dimethyl-1-(p-Isopropylphenyl)-non-1-ene

HRID 280069Notes

Reaction equation

HRID 280069 reaction equation
[Na].N.[CH3:3][CH:4]([CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])[CH2:5][CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:16])[CH3:15])=[CH:10][CH:9]=1>O1CCCC1>[CH3:3][CH:4]([CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:5][CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:15])[CH3:16])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5360545SodiumHCID 544310941-(4,8-Dimethylnona-1,7-dien-1-yl)-4-(propan-2-yl)benzene

Product 1

HCID 537879604,8-Dimethyl-1-(p-Isopropylphenyl)-non-1-ene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 16 g (0.7 g at) of sodium in 600 ml of liquid ammonia was added dropwise a solution of 93 g (0.34 mol.) of 4,8-dimethyl-1-(p-isopropylphenyl)nona-1,7-diene in 125 ml of anhydrous tetrahydrofuran. Total addition time was one hour. The excess sodium was destroyed by the cautious addition of methanol. Then 200 ml of hexane were added and the ammonia was allowed to evaporate. To the residue a saturated solution of NH4Cl was added cautiously. The organic layer was separated, and the aqueous layer was diluted with water and extracted twice with hexane. The combined hexane layers were washed with water, dilute HCl, brine and then dried. Evaporation of the hexane and distillation of the residue yielded the title product. Yield was 88 g (94%), bp 130°-135° C/0.1 mm. nD25 =1.4938.

Workup

  1. customThe excess sodium was destroyed by the cautious addition of methanol
  2. additionThen 200 ml of hexane were added
  3. customto evaporate
  4. additionTo the residue a saturated solution of NH4Cl was added cautiously
  5. customThe organic layer was separated
  6. additionthe aqueous layer was diluted with water
  7. extractionextracted twice with hexane
  8. washThe combined hexane layers were washed with water, dilute HCl, brine
  9. customdried
  10. customEvaporation of the hexane and distillation of the residue

Sources & evidence

ORD record
ord-ca1ac39a6d37432eaf575778c5438dd5
Source dataset
uspto-grants-1986_05
Patent number
USRE032147

Reaction notes

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