1,2,3,4,5,6,7,8-octapropyl-9,10-dihydroanthracene → 1,2,3,4,5,6,7,8-octapropylanthracene

HRID 600131Notes

Reaction equation

HRID 600131 reaction equation
[CH2:1]([C:4]1[C:17]2[CH2:16][C:15]3[C:10](=[C:11]([CH2:27][CH2:28][CH3:29])[C:12]([CH2:24][CH2:25][CH3:26])=[C:13]([CH2:21][CH2:22][CH3:23])[C:14]=3[CH2:18][CH2:19][CH3:20])[CH2:9][C:8]=2[C:7]([CH2:30][CH2:31][CH3:32])=[C:6]([CH2:33][CH2:34][CH3:35])[C:5]=1[CH2:36][CH2:37][CH3:38])[CH2:2][CH3:3]>C1C=CC=CC=1>[CH2:30]([C:7]1[C:8]2[C:17](=[CH:16][C:15]3[C:10]([CH:9]=2)=[C:11]([CH2:27][CH2:28][CH3:29])[C:12]([CH2:24][CH2:25][CH3:26])=[C:13]([CH2:21][CH2:22][CH3:23])[C:14]=3[CH2:18][CH2:19][CH3:20])[C:4]([CH2:1][CH2:2][CH3:3])=[C:5]([CH2:36][CH2:37][CH3:38])[C:6]=1[CH2:33][CH2:34][CH3:35])[CH2:31][CH3:32]

Participants

3

Reactant 1

HCID 114323181,2,3,4,5,6,7,8-octapropyl-9,10-dihydroanthracene

Product 1

HCID 114550891,2,3,4,5,6,7,8-octapropylanthraceneYield 79.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

After 2,3-dichloro-5,6-dicyanoquinone (0.100 g, 0.440 mmol) was added to a solution of 1,2,3,4,5,6,7,8-octapropyl-9,10-dihydroanthracene (0.208 g, 0.400 mmol) in benzene (5 ml), the mixture was refluxed for an hour with heating. The reaction mixture was filtered to remove hydroquinone and purified by silica gel column chromatography (ethyl acetate/hexane, 99/1) to give the title compound (0.164 g) as a white solid. The isolation yield was 79%.

Workup

  1. temperaturethe mixture was refluxed for an hour
  2. temperaturewith heating
  3. filtrationThe reaction mixture was filtered
  4. customto remove hydroquinone
  5. custompurified by silica gel column chromatography (ethyl acetate/hexane, 99/1)

Sources & evidence

ORD record
ord-8065783f97954cc58ed3954c39c8ddcd
Source dataset
uspto-grants-2011_03
Patent number
US07901594B2

Reaction notes

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