Sodium Hydroxide → HCID 178442477, compound

HRID 1737151Notes

Reaction equation

HRID 1737151 reaction equation
[OH-].[Na+].C([O:6][C:7]1[C:8](=[O:24])[C:9]2[C:14]([C:15](=[O:23])[C:16]=1[CH2:17][CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:13][CH:12]=[CH:11][CH:10]=2)(=O)C>C1COCC1>[CH3:20][C:19]([CH3:22])([CH3:21])[CH2:18][CH2:17][C:16]1[C:15](=[O:23])[C:14]2[C:9]([C:8](=[O:24])[C:7]=1[OH:6])=[CH:10][CH:11]=[CH:12][CH:13]=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21841785HCID 21841785, compound

Product 1

HCID 178442477HCID 178442477, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide solution (1M; 100 ml) was added to a solution of 2-ethanoyloxy-3-(3,3-dimethylbutyl)-naphthalene-1,4-dione (3.5 g)(see Example 44) in THF (100 ml) at room temperature and stirred for 4 hours. The THF was removed under vacuum and the resultant solution was washed with diethyl ether (3x). The aqueous layer was acidified then extracted with diethyl ether (x3), the combined extracts washed with water, dried over magnesium sulphate then evaporated to dryness under vacuum to yield 3 g title compound.

Workup

  1. customThe THF was removed under vacuum
  2. washthe resultant solution was washed with diethyl ether (3x)
  3. extractionThe aqueous layer was acidified then extracted with diethyl ether (x3)
  4. washthe combined extracts washed with water
  5. dry with materialdried over magnesium sulphate
  6. customthen evaporated to dryness under vacuum

Sources & evidence

ORD record
ord-e42858a208cf4550b9dd903ff886690a
Source dataset
uspto-grants-1999_10
Patent number
US05962002

Reaction notes

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