Acetone → HCID 14397959, compound

HRID 652611Notes

Reaction equation

[Cl:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([OH:17])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[C:5]([Cl:19])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:26][C:27]1[CH:34]=[C:33]([CH3:35])[CH:32]=[C:31]([CH3:36])[C:28]=1[CH2:29]Cl.CC(C)=O>C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>[Cl:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([O:17][CH2:29][C:28]4[C:31]([CH3:36])=[CH:32][C:33]([CH3:35])=[CH:34][C:27]=4[CH3:26])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[C:5]([Cl:19])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 10 °C

Procedure

A mechanically stirred mixture of 550.6 g (1.88 mol) of 1,4-dichloro-5-hydroxy-9,10-anthracenedione (1), 413.4 g (2.14 mol) of anhydrous cesium carbonate, 444 g, (2.4 mol) of 2,4,6-trimethylbenzyl chloride, 7.06 l of acetone, and 2.31 l of N,N-dimethylformamide was heated at reflux for 23 hr. During this period, additional portions of 2,4,6-trimethylbenzyl chloride (2.5 hr, 31.7 g; 6.5 hr, 63.4 g; 20 hr, 31.7 g) and one portion of cesium carbonate (20 hr, 4.8 g) were added. The mixture was cooled to 10° C. The precipitate was collected by filtration, washed successively with hot water and methanol, then dried at 7-9 mm/50° C./20 hr to leave 621 g (78%) of 11, mp 216°-218° C., 97.9% pure by HPLC.

Workup

temperaturewas heated
temperatureat reflux for 23 hr
waitDuring this period
filtrationThe precipitate was collected by filtration
washwashed successively with hot water and methanol
customdried at 7-9 mm/50° C./20 hr

Sources & evidence

ORD record: ord-c61b9c807bce4ee28cc00901c41c3fb3
Source dataset: uspto-grants-1987_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04672129

Reaction notes

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