Sodium Valerate → 9-Valeryloxyacetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione

HRID 464008Notes

Reaction equation

HRID 464008 reaction equation
Br[CH2:2][C:3]([C:5]1([OH:27])[CH2:22][C:21]2[C:20]([OH:23])=[C:19]3[C:10]([C:11](=[O:25])[C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=4[C:18]3=[O:24])=[C:9]([OH:26])[C:8]=2[CH2:7][CH2:6]1)=[O:4].[C:28]([O-:34])(=[O:33])[CH2:29][CH2:30][CH2:31][CH3:32].[Na+]>CC(C)=O>[C:28]([O:34][CH2:2][C:3]([C:5]1([OH:27])[CH2:22][C:21]2[C:20]([OH:23])=[C:19]3[C:10]([C:11](=[O:25])[C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=4[C:18]3=[O:24])=[C:9]([OH:26])[C:8]=2[CH2:7][CH2:6]1)=[O:4])(=[O:33])[CH2:29][CH2:30][CH2:31][CH3:32]

Participants

4

Reactant 2

HCID 3669864Sodium ValerateHCID 131462669-Bromoacetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione

Product 1

HCID 132929939-Valeryloxyacetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 9-bromoacetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione (1.00 g) obtained in Reference Example 1-(1), sodium valerate (1.44 g) and acetone (50 ml) was stirred under reflux for 5 hours, cooled to room temperature and concentrated under reduced pressure. The residue was triturated with an adequate quantity of ether, and solid substances were filtered to give reddish crystals of 9-valeryloxyacetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione. M.P., 170°-172° C.

Workup

  1. temperatureunder reflux for 5 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was triturated with an adequate quantity of ether, and solid substances
  4. filtrationwere filtered

Sources & evidence

ORD record
ord-9379d6b930244f0688c9ed4bd3ef32b7
Source dataset
uspto-grants-1985_10
Patent number
US04545936

Reaction notes

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