Hydrochloric Acid → HCID 57747229, compound

HRID 1163474Notes

Reaction equation

HRID 1163474 reaction equation
[CH3:1]/[C:2](/[CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])=[CH:3]\[CH2:4][OH:5].[OH-].[K+].Br[CH2:15][C:16]([C:18]1[CH:23]=[C:22]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:21]([OH:28])=[C:20]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:19]=1)=[O:17].Cl>O.CN1CCCC1=O>[C:24]([C:22]1[CH:23]=[C:18]([C:16](=[O:17])[CH2:15][O:5][CH2:4]/[CH:3]=[C:2](\[CH3:1])/[CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])[CH:19]=[C:20]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:21]=1[OH:28])([CH3:27])([CH3:25])[CH3:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 6161612-Bromo-1-[3,5-di(tert-butyl)-4-hydroxyphenyl]ethan-1-oneHCID 637566Geraniol

Product 1

HCID 57747229HCID 57747229, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 9.6 g (62 mmol) of (E)-3,7-dimethyl-octa-2,6-dien-1-ol, 8.4 g (150 mmol) of potassium hydroxide and 20 ml of n-methylpyrrolidone are stirred for one hour at room temperature. Then 10.0 g (33 mmol) of 2-bromo-1-(3,5-di-tert-butyl-4-hydroxyphenyl)-ethanone is added in portions and stirring is continued at room temperature for 20 hours. After the addition of 30 ml of water the mixture is neutralized with 6N hydrochloric acid while cooling with an ice bath and then extracted with ethyl acetate. The organic phases are washed twice with brine, dried over sodium sulfate and evaporated. The residue is purified by column chromatography and crystallisation of the pure fractions from hexane gives 6.1 g (50%) of compound 116; m.p. 50° C.

Workup

  1. stirringstirring
  2. waitis continued at room temperature for 20 hours
  3. temperaturewhile cooling with an ice bath
  4. extractionextracted with ethyl acetate
  5. washThe organic phases are washed twice with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe residue is purified by column chromatography and crystallisation of the pure fractions from hexane

Sources & evidence

ORD record
ord-f9a21b5c4447488dbea7fefdcf1915cf
Source dataset
uspto-grants-2010_10
Patent number
US07820865B2

Reaction notes

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