HCID 20491281, compound → HCID 20491279, compound

HRID 435210Notes

Reaction equation

HRID 435210 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[CH:5]=[C:4]([CH3:13])[C:3]=1[O:14][CH3:15].[H][H]>C(O)(C)C.[Pd]>[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[CH:5]=[C:4]([CH3:13])[C:3]=1[O:14][CH3:15]

Participants

5

Reactant 2

HCID 20491281HCID 20491281, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20491279HCID 20491279, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A solution of 2,6-dimethyl-4-(3-methyl-2-butenyl)anisole (10 g, 0.05 mol) in isopropanol (20 mL), together with 5% palladium on carbon (0.1 g) was hydrogenated in a Parr apparatus until the theoretical amount of hydrogen had been consumed. The catalyst was removed by filtration and the solvent evaporated to give a clear residue which was fractionated to afford 7.1 g of the desired product, bp 102°-105° C. (2 mm). NMR (CDCl3) δ0.9 (6H, d), 1.1-2.0 (3H, m), 2.2 (6H, s), 2.5 (2H, t), 3.7 (3H, s), 6.85 (2H, s). IR (film) 3000, 1225, 1025, 870 cm-1. MS (m/e) 206 (M+), 149, 150, 135, 191.

Workup

  1. customhad been consumed
  2. customThe catalyst was removed by filtration
  3. customthe solvent evaporated
  4. customto give a clear residue which

Sources & evidence

ORD record
ord-3648b5d5fc8143a5886379dae33899ef
Source dataset
uspto-grants-1983_08
Patent number
US04400545

Reaction notes

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