Hydrochloric Acid → HCID 66720751, compound

HRID 883820Notes

Reaction equation

HRID 883820 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:48])[C:13]4[C:22]([C:23](=[O:35])[C:24]=3[CH:25]=2)=[CH:21][C:20]2[C:15](=[CH:16][C:17]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[C:18]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[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>O1CCCC1>[CH2:36]([C:18]1[C:17]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[CH:16][C:15]2[C:20](=[CH:21][C:22]3[CH:23]([OH:35])[C:24]4[C:11]([CH:12]([OH:48])[C:13]=3[CH:14]=2)=[CH:10][C:9]2[C:26](=[CH:27][C:28]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH:8]=2)[CH:25]=4)[CH:19]=1)[CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23154340HCID 23154340, compoundHCID 23664628Lithiumtriethylborohydride

Product 1

HCID 66720751HCID 66720751, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 649 mg of 2,3,9,10-tetra(n-hexyl)-6,13-pentacenequinone dissolved in 30 mL of tetrahydrofuran (THF) was added to 5 mL of a 1 mol/1000 mL THF solution of lithium triethylborohydride, and the mixture was heated for 12 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 2,3,9,10-tetra(n-hexyl)-6,13-dihydro-6,13-dihydroxypentac ene almost stoichiometrically (see the following reaction formula).

Workup

  1. temperaturethe mixture was heated for 12 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-9aa6d4c2df124075a164700ec307f59e
Source dataset
uspto-grants-2012_08
Patent number
US08236998B2

Reaction notes

Loading…