Aluminum sec-butoxide → 2,9-Dihexylpentacene

HRID 488981Notes

Reaction equation

CC(CC)[O-].CC(CC)[O-].CC(CC)[O-].[Al+3].[CH2:17]([C:23]1[CH:24]=[CH:25][C:26]2[CH:27]=[C:28]3[C:41]([C:42](=O)[C:43]=2[CH:44]=1)=[CH:40][C:39]1[C:30]([C:31](=O)[C:32]2[C:37]([CH:38]=1)=[CH:36][CH:35]=[C:34]([CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH:33]=2)=[CH:29]3)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>C1(O)CCCCC1>[CH2:17]([C:23]1[CH:24]=[CH:25][C:26]2[C:43](=[CH:42][C:41]3[C:28]([CH:27]=2)=[CH:29][C:30]2[C:39](=[CH:38][C:37]4[C:32]([CH:31]=2)=[CH:33][C:34]([CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])=[CH:35][CH:36]=4)[CH:40]=3)[CH:44]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

Conditions

Temperature: 145 °C

Procedure

A mixture of 5.69 grams of aluminum tri(sec-butoxide) and 49.1 mLs of cyclohexanol was made. To this was added 2.21 grams 3,10-Dihexylpentacene-5,12-dione. The reaction mixture was heated to 145° C. for 24 hours. The mixture was cooled to room temperature and the solid isolated by centrifugation. The solid was stirred with 40 mLs of cyclohexanol and centrifuged two times. The solid was collected by filtration and washed with THF to give 2,9-dihexylpentacene.

Workup

temperatureThe mixture was cooled to room temperature
customthe solid isolated by centrifugation
filtrationThe solid was collected by filtration
washwashed with THF

Sources & evidence

ORD record: ord-6f4cfd59a8d54b509d5f65523dcba468
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06974877B2

Reaction notes

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