pentacene-5,7(12H,14H)-dione → Pentacene

HRID 488977

Reaction equation

HRID 488977 reaction equation
[CH:1]1[C:22]2[CH2:21][C:20]3[C:7](=[CH:8][C:9]4[CH2:10][C:11]5[C:16]([C:17](=O)[C:18]=4[CH:19]=3)=[CH:15][CH:14]=[CH:13][CH:12]=5)[C:6](=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C1C2CC3C(=CC4C(=O)C5C(CC=4C=3)=CC=CC=5)C(=O)C=2C=CC=1>COCCOCCOC>[CH:4]1[C:5]2[C:22](=[CH:21][C:20]3[C:7]([CH:6]=2)=[CH:8][C:9]2[C:18](=[CH:17][C:16]4[C:11]([CH:10]=2)=[CH:12][CH:13]=[CH:14][CH:15]=4)[CH:19]=3)[CH:1]=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 22269435pentacene-5,7(12H,14H)-dioneHCID 222694837,14-Dihydropentacene-5,12-dione

Product 1

HCID 8671Pentacene

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1.0 gram of 7,14-dihydropentacene-5,12-dione and pentacene-5,7(12H,14H)-dione, and 10 mL of 2-methoxyethyl ether was stirred and flushed with nitrogen for 15 minutes. To this was added 1.03 grams of sodium borohydride and stirring was continued at room temperature overnight. To the mixture was added 10 mL of 2-methoxyethyl ether and 6.3 mL of methanol and stirring was continued for 1.5 hours at room temperature. To the mixture was added 15 mL of acetic acid and 10 mL of concentrated hydrochloric acid. The mixture was stirred for one hour at room temperature and heated to 60° C. for one hour. To the mixture was added 50 mL of water, and the resulting solid was isolated by filtration and washed with water. The solid was washed with tetrahydrofuran until a pale filtrate resulted. The solid was washed with heptane and dried to give pentacene.

Workup

  1. customflushed with nitrogen for 15 minutes
  2. additionTo this was added 1.03 grams of sodium borohydride
  3. stirringstirring
  4. additionTo the mixture was added 10 mL of 2-methoxyethyl ether and 6.3 mL of methanol
  5. stirringstirring
  6. waitwas continued for 1.5 hours at room temperature
  7. additionTo the mixture was added 15 mL of acetic acid and 10 mL of concentrated hydrochloric acid
  8. stirringThe mixture was stirred for one hour at room temperature
  9. additionTo the mixture was added 50 mL of water
  10. customthe resulting solid was isolated by filtration
  11. washwashed with water
  12. washThe solid was washed with tetrahydrofuran until a pale filtrate
  13. customresulted
  14. washThe solid was washed with heptane
  15. customdried

Sources & evidence

ORD record
ord-276ab823f2a94184bdeb6d78985d82de
Source dataset
uspto-grants-2005_12
Patent number
US06974877B2

Linked notes

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