Hydrochloric Acid → HCID 57747226, compound

HRID 1163473Notes

Reaction equation

HRID 1163473 reaction equation
[OH-].[K+].Br[CH:4]([CH3:22])[C:5]([C:7]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]([OH:17])=[C:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:8]=1)=[O:6].Cl.O.[CH2:25]([OH:27])[CH3:26]>CN1CCCC1=O>[C:18]([C:9]1[CH:8]=[C:7]([C:5](=[O:6])[CH:4]([O:27][CH2:25][CH3:26])[CH3:22])[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]=1[OH:17])([CH3:21])([CH3:20])[CH3:19]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 14797Potassium HydroxideHCID 13173168HCID 13173168, compound

Product 1

HCID 57747226HCID 57747226, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

6.6 g (117 mmol) of potassium hydroxide are dissolved in 130 ml of ethanol and stirred for one hour. Then 10.0 g (29.3 mmol) of 2-bromo-1-(3,5-di-tert-butyl-4-hydroxyphenyl)-propan-1-one dissolved in 20 ml of n-methylpyrrolidone is added at room temperature while stirring. After stirring for 20 hours the reaction mixture is cooled with an ice bath and 5 ml of concentrated hydrochloric acid and 150 ml of water is added. Then ethanol is evaporated, 200 ml of ethylacetate added and the water phase split off. The organic phase is washed with 100 ml of brine, dried over sodium sulfate and evaporated. The residue is purified by column chromatography and crystallisation of the pure fractions from hexane to give 4.1 g (45%) of compound 115; m.p. 64° C.

Workup

  1. additionis added at room temperature
  2. stirringwhile stirring
  3. stirringAfter stirring for 20 hours the reaction mixture
  4. temperatureis cooled with an ice bath
  5. customThen ethanol is evaporated
  6. addition200 ml of ethylacetate added
  7. customthe water phase split off
  8. washThe organic phase is washed with 100 ml of brine
  9. dry with materialdried over sodium sulfate
  10. customevaporated
  11. customThe residue is purified by column chromatography and crystallisation of the pure fractions from hexane

Sources & evidence

ORD record
ord-c560f89e8f0740bcbe3343255bb1c62e
Source dataset
uspto-grants-2010_10
Patent number
US07820865B2

Reaction notes

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