12-Methyl-1,2,3,4-tetrahydrochrysene → 6-Methylchrysene

HRID 399643

Reaction equation

HRID 399643 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:13](=[C:14]3[C:19]=1[CH2:18][CH2:17][CH2:16][CH2:15]3)[CH:12]=[CH:11][C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=1>[Pd].COCCOCCOCCOC>[CH3:1][C:2]1[CH:3]=[C:4]2[C:13](=[C:14]3[C:19]=1[CH:18]=[CH:17][CH:16]=[CH:15]3)[CH:12]=[CH:11][C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=1

Participants

4

Reactant 1

HCID 1111835212-Methyl-1,2,3,4-tetrahydrochrysene

Product 1

HCID 155646-MethylchryseneYield 73.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8189TriglymeSolvent

Conditions

Temperature
210 °C

Procedure

A mixture of palladium on carbon (10%, 5.0 g) and 6-methyl-7,8,9,10-tetrahydro-chrysene (64.0 g, 0.24 mol) in triglyme (290 mL) was heated at 210° C. under a slow nitrogen stream. The progress of the reaction was monitored by NMR analysis that showed the reaction was 72% complete after 4 hours. The heating was discontinued after 18 hours when essentially all of the starting material had been consumed. The mixture was cooled to 100° C. and filtered to remove the catalyst. The solution was then cooled further to 0° C., and filtered to give 42.9 g (68% yield) of 6-methylchrysene. The filtrate was diluted with water (300 mL) and filtered to give an additional 15.5 g (93% combined yield) of 6-methylchrysene. 1H NMR (CDCl3) 2.86 (s, 3 H), 7.6 (m, 4 H), 7.9 (m, 2 H), 8.1 (m, 1 H), 8.55 (s, 1 H), 8.65 (m, 1 H), 8.8 (m, 2 H).

Workup

  1. customcomplete after 4 hours
  2. customwhen essentially all of the starting material had been consumed
  3. temperatureThe mixture was cooled to 100° C.
  4. filtrationfiltered
  5. customto remove the catalyst
  6. temperatureThe solution was then cooled further to 0° C.
  7. filtrationfiltered

Sources & evidence

ORD record
ord-468ccd8b1c86445097e50c04c66a66d0
Source dataset
uspto-grants-1998_10
Patent number
US05821387

Linked notes

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