HCID 20437930, compound → 1-(8-Methoxy-4,8-dimethylnonyl)-4-(1-methylethyl)benzene

HRID 1980010Notes

Reaction equation

HRID 1980010 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10](O)[CH2:11][CH2:12][CH:13]([CH3:22])[CH2:14][CH2:15][CH2:16][C:17]([CH3:21])([O:19][CH3:20])[CH3:18])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[H][H]>CO.Cl.[Pd]>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][CH:13]([CH3:22])[CH2:14][CH2:15][CH2:16][C:17]([CH3:21])([O:19][CH3:20])[CH3:18])=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 20437930HCID 20437930, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 620711-(8-Methoxy-4,8-dimethylnonyl)-4-(1-methylethyl)benzene

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

The reaction mixture containing 1-(p-isopropylphenyl)-4,8-dimethyl-8-methoxynonan-1-ol as obtained above (Example III) (9.9 g) was submitted to hydrogenolysis by dissolution in an acidic lower alkanol, e.g., methanol (50 ml) and conc. HCl (1 ml) and was then hydrogenated with H2 in the presence of 5% Pd-C (0.4 g). After uptake of hydrogen ceased, the catalyst was removed by filtration with the aid of a filter aid (Celite). The filtrate was washed with aq. NaHCO3, brine and dried over MgSO4. Evaporation of solvent left a yellow oil (8.4 g). Distillation gave the desired product (1-(p-isopropylphenyl)-4,8-dimethyl-8-methoxynonane) (2.8 g, bp. 120°-125°/0.05 torr). The NMR spectrum showed the following signals 1.08 (6H, s), 1.22 (6H, d, J.=6.5 Hz): (CDCl3) 0.88 (3H, d, J=6.5 Hz), 2.60 (2H, t, J=7 Hz), 2.90 (1H, m), 3.14 (3H, s), 7.10 (4H, s).

Workup

  1. customas obtained above (Example III) (9.9 g)
  2. customthe catalyst was removed by filtration with the aid of a filter aid (Celite)
  3. washThe filtrate was washed with aq. NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. customEvaporation of solvent
  6. waitleft a yellow oil (8.4 g)
  7. distillationDistillation

Sources & evidence

ORD record
ord-bcb56a3a87504cf2acdcabc53acbe1ca
Source dataset
uspto-grants-1984_11
Patent number
US04484007

Reaction notes

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