Lithium Hydroxide → HCID 58045815, compound

HRID 1524585Notes

Reaction equation

HRID 1524585 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]([C:15]1[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:18]=[C:17](C(=O)C)[CH:16]=1)(=[O:14])[CH3:13].[OH-].[Li+].[OH-].[Na+]>ClCCl>[C:21]([C:19]1[CH:20]=[C:15]([C:12](=[O:14])[CH3:13])[CH:16]=[C:17]([OH:9])[CH:18]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 3939Lithium HydroxideHCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 19601772HCID 19601772, compound

Product 1

HCID 58045815HCID 58045815, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperbenzoic acid (382 g, 2.21 mol) was added to a solution of 1,3-bisacetyl-5-tert-butylbenzene (O4.106; 169 g, 776 mmol) in dichloromethane (1.7 l). The resulting suspension was heated to reflux temperature for 24 h. Once the suspension had cooled, the solids were filtered off and the filtrate was admixed with saturated aqueous NaHSO3 solution (500 ml). The phases were separated, the organic phase was dried (MgSO4) and the solvent was removed under reduced pressure. The residue was dissolved in THF (500 ml) and admixed with lithium hydroxide (34.9 g, 1.46 mol). After 4 h at RT, aqueous sodium hydroxide solution (1 M, 500 ml) was added and the mixture was washed with MtB ether (3×500 ml). The aqueous phase was acidified (pH 3) with HCl (1 M), and extracted with EA (3×500 ml). The combined organic phases were dried (MgSO4), and the solvent was removed under reduced pressure. The crude product was purified by preparative HPLC (met. C). The product was obtained as a colorless oil which crystallized slowly (36.5 g).

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux temperature for 24 h
  3. temperatureOnce the suspension had cooled
  4. filtrationthe solids were filtered off
  5. customThe phases were separated
  6. dry with materialthe organic phase was dried (MgSO4)
  7. customthe solvent was removed under reduced pressure
  8. dissolutionThe residue was dissolved in THF (500 ml)
  9. washthe mixture was washed with MtB ether (3×500 ml)
  10. extractionextracted with EA (3×500 ml)
  11. dry with materialThe combined organic phases were dried (MgSO4)
  12. customthe solvent was removed under reduced pressure
  13. customThe crude product was purified by preparative HPLC (met. C)
  14. customThe product was obtained as a colorless oil which
  15. customcrystallized slowly (36.5 g)

Sources & evidence

ORD record
ord-d629e50ca5254746af21665ab3df90d0
Source dataset
uspto-grants-2015_07
Patent number
US09079906B2

Reaction notes

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