Potassium Hydroxide → HCID 86674065, compound

HRID 876106Notes

Reaction equation

HRID 876106 reaction equation
C([O:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]2[C:12]3[CH:13]=[CH:14][CH:15]=[C:16]4[C:27]=3[C:20]([C:21]3[C:26]=2[C:25]=1[CH:24]=[CH:23][CH:22]=3)=[CH:19][CH:18]=[C:17]4[C:28]([O:30]CC(C)C)=[O:29])=[O:7])C(C)C.[OH-].[K+:36]>CCO>[CH:19]1[C:20]2=[C:27]3[C:12]([C:11]4[C:26]5[C:25](=[CH:24][CH:23]=[CH:22][C:21]2=5)[C:8]([C:6]([O-:7])=[O:5])=[CH:9][CH:10]=4)=[CH:13][CH:14]=[CH:15][C:16]3=[C:17]([C:28]([O-:30])=[O:29])[CH:18]=1.[K+:36].[K+:36]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 75973Diisobutyl 3,9-perylenedicarboxylate

Product 1

HCID 86674065HCID 86674065, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,9-Perylenedicarboxylic acid diisobutyl ester (500 mg, 1.1 mmol, 1 eq) was suspended in 200 mL EtOH, and 1 M aq. KOH (7 mL, 3.3 mmol, 3 eq) was added. The reaction mixture was refluxed for 16 h. The precipitate was filtered off and washed with EtOH as well as DCM to provide the title compound as a yellow powder (369 mg, 0.9 mmol, 80%). 1H NMR (400 MHz, MeOD, 333K) δ 6.87-6.82 (m, 2H, PDA aromatic H), 6.76 (dd, J=9.7, 7.5 Hz 4H, PDA aromatic H), 6.17 (d, J=7.7 Hz 4H, PDA aromatic H), 5.99 (ddd, J=8.6, 7.6, 1.2 Hz 4H, PDA aromatic H). HRMS (ESI): calcd. mass for C22H11O4−: ([M−H]−) 339.0663. found: 339.0653.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. filtrationThe precipitate was filtered off
  3. washwashed with EtOH as well as DCM

Sources & evidence

ORD record
ord-476d00060a7448509003d3319c871ff1
Source dataset
uspto-grants-2015_03
Patent number
US08986842B2

Reaction notes

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