Benzene → HCID 21490623, compound

HRID 1657889Notes

Reaction equation

HRID 1657889 reaction equation
[CH2:1]=[CH:2][CH:3]1[CH2:8][CH:7]=[CH:6][CH2:5][CH2:4]1.[CH3:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[C:16](=[O:21])[CH:15]=[CH:14][C:13]2=[O:22].C1C=CC=CC=1>[Pd].CO>[CH2:4]([CH:5]1[C:14]2[C:13](=[O:22])[C:12]3[C:17](=[CH:18][C:19]([CH3:20])=[C:10]([CH3:9])[CH:11]=3)[C:16](=[O:21])[C:15]=2[CH2:8][CH2:7][CH2:6]1)[CH2:3][CH2:2][CH3:1]

Participants

5

Reactant 2

HCID 241BenzeneHCID 131710320HCID 131710320, compound

Product 1

HCID 21490623HCID 21490623, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 3.0 g. sample of the butadiene dimer-6,7-dimethylnaphthoquinone adduct was dissolved in 100 ml. benzene. After the addition of 0.30 g. 10% Pd/C catalyst, the mixture was hydrogenated at 35 psi for four hours. After removal of catalyst by filtration, five drops DBN were added and the mixture was stirred overnight while exposed to air. The benzene was then blown off with air and the residue chromatographed on acidic alumina with a 9:1 benzene-ethyl acetate solution. The crude product (1.1 g.; 36% yield) was recrystallized from methanol to give an analytical sample with m.p. 88°-90°C.

Workup

  1. additionAfter the addition of 0.30 g
  2. customAfter removal of catalyst
  3. filtrationby filtration, five drops DBN
  4. additionwere added
  5. customthe residue chromatographed on acidic alumina with a 9:1 benzene-ethyl acetate solution

Sources & evidence

ORD record
ord-b4a5073c25204bc2bf7da531eaa001e5
Source dataset
uspto-grants-1976_06
Patent number
US03962288

Reaction notes

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