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Acetone → HCID 14397959, compound

HRID 652611
Notes
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Reaction equation

HRID 652611 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 180AcetoneHCID 10796Cesium carbonateHCID 741082,4,6-Trimethylbenzyl chloride2×HCID 108916751,4-dichloro-5-hydroxy-9,10-Anthracenedione

Product 1

HCID 14397959HCID 14397959, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 10796
Cesium carbonate
Catalyst
HCID 6228DimethylformamideSolvent

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

  1. temperaturewas heated
  2. temperatureat reflux for 23 hr
  3. waitDuring this period
  4. filtrationThe precipitate was collected by filtration
  5. washwashed successively with hot water and methanol
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes