Hydrochloric Acid → 4-Isobutylresorcinol

HRID 2097296Notes

Reaction equation

HRID 2097296 reaction equation
ClC(OCC)=O.[OH:7][C:8]1[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][C:9]=1[C:15](=O)[CH:16]([CH3:18])[CH3:17].C(N(CC)CC)C.[BH4-].[Na+].[OH-].[Na+].Cl>C1COCC1.O>[CH2:15]([C:9]1[CH:10]=[CH:11][C:12]([OH:14])=[CH:13][C:8]=1[OH:7])[CH:16]([CH3:18])[CH3:17]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 159157311-(2,4-Dihydroxyphenyl)-2-methylpropan-1-one

Product 1

HCID 139510854-Isobutylresorcinol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl chloroformate (3 eq) was added slowly to a cooled (0° C.) solution of 1-(2,4-dihydroxy-phenyl)-2-methyl-propan-1-one (1 eq) and triethylamine (3 eq) in THF. The mixture was warmed to ambient temperature and stirred for three hours before being filtered and the solids washed with cold THF. The combined filtrates were cooled to 0° C. and sodium borohydride (4 eq) in a volume of water equal to the THF filtrates added slowly. The mixture was warmed to ambient temperature, stirred for three hours and diluted with water. The mixture was twice extracted with diethyl ether, the combined extracts concentrated to dryness and re-suspended in 10% aqueous sodium hydroxide solution (4 eq). After refluxing for 90 minutes, the mixture was cooled, acidified with 5M aq HCl and twice extracted with diethyl ether. The organic extracts were dried over magnesium sulphate, filtered and concentrated to dryness to give 4-isobutyl-benzene-1,3-diol as a cloudy oil, which was used without further purification.

Workup

  1. filtrationbefore being filtered
  2. washthe solids washed with cold THF
  3. temperatureThe combined filtrates were cooled to 0° C.
  4. temperatureThe mixture was warmed to ambient temperature
  5. stirringstirred for three hours
  6. extractionThe mixture was twice extracted with diethyl ether
  7. concentrationthe combined extracts concentrated to dryness
  8. temperatureAfter refluxing for 90 minutes
  9. temperaturethe mixture was cooled
  10. extractiontwice extracted with diethyl ether
  11. dry with materialThe organic extracts were dried over magnesium sulphate
  12. filtrationfiltered
  13. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-e3aa500e5c6b49e4b137e1c53512d89b
Source dataset
uspto-grants-2013_05
Patent number
US08450310B2

Reaction notes

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