Hydrochloric Acid → HCID 66720600, compound

HRID 883822Notes

Reaction equation

HRID 883822 reaction equation
[CH2:1]([C:4]1[C:25]([CH2:26][CH2:27][CH3:28])=[CH:24][C:23]2[C:6](=[CH:7][C:8]3[C:9](=[O:30])[C:10]4[C:19]([C:20](=[O:29])[C:21]=3[CH:22]=2)=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=4)[CH:5]=1)[CH2:2][CH3:3].C([BH-](CC)CC)C.[Li+].Cl>C1COCC1>[OH:29][CH:20]1[C:19]2[C:10](=[CH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:9]([OH:30])[C:8]2[CH:7]=[C:6]3[C:23]([CH:24]=[C:25]([CH2:26][CH2:27][CH3:28])[C:4]([CH2:1][CH2:2][CH3:3])=[CH:5]3)=[CH:22][C:21]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23156926HCID 23156926, compoundHCID 23664628Lithiumtriethylborohydride

Product 1

HCID 66720600HCID 66720600, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 314 mg of 2,3-di(n-propyl)-6,13-pentacenequinone dissolved in 60 mL of THF was added to 6 mL of a 1 mol/1000 mL THF solution of lithium triethylborohydride, and the mixture was heated for 20 hours under reflux in a nitrogen atmosphere. The resulting solution was neutralized with diluted aqueous hydrochloric acid, and the organic phase was separated, concentrated and dried under a vacuum to produce 6,13-dihydro-6,13-dihydroxy-2,3-di(n-propyl)pentacene almost stoichiometrically.

Workup

  1. temperaturethe mixture was heated for 20 hours
  2. temperatureunder reflux in a nitrogen atmosphere
  3. customthe organic phase was separated
  4. concentrationconcentrated
  5. customdried under a vacuum

Sources & evidence

ORD record
ord-8bf80ea694104993950592d759a7516a
Source dataset
uspto-grants-2012_08
Patent number
US08236998B2

Reaction notes

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