Hydrochloric Acid → HCID 66720718, compound

HRID 1640086Notes

Reaction equation

HRID 1640086 reaction equation
[CH2:1]([C:7]1[C:28]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:27][C:26]2[C:9](=[CH:10][C:11]3[C:12](=[O:36])[C:13]4[C:22]([C:23](=[O:35])[C:24]=3[CH:25]=2)=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=4)[CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C([BH-](CC)CC)C.[Li+].Cl>C1COCC1>[CH2:29]([C:28]1[C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:8][C:9]2[C:26](=[CH:25][C:24]3[CH:23]([OH:35])[C:22]4[C:13]([CH:12]([OH:36])[C:11]=3[CH:10]=2)=[CH:14][C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=4)[CH:27]=1)[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23664628LithiumtriethylborohydrideHCID 66720665HCID 66720665, compound

Product 1

HCID 66720718HCID 66720718, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 334 mg of 2,3-dihexyl-6,13-pentacenequinone dissolved in 50 mL of THF was added to 11 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 2,3-dihexyl-6,13-dihydro-6,13-dihydroxypentacene 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-c078039610614f92ace9a165d2651f0e
Source dataset
uspto-grants-2012_02
Patent number
US08110714B2

Reaction notes

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