Hydrochloric Acid → 1-(2,4-Dihydroxyphenyl)-2-methyl-1-butanone

HRID 345737Notes

Reaction equation

HRID 345737 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].Cl.O.C(Cl)(Cl)Cl.[CH3:15][CH2:16][C@@H:17]([C:19](O)=[O:20])[CH3:18]>[Cl-].[Zn+2].[Cl-]>[OH:2][C:1]1[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][C:8]=1[C:19](=[O:20])[CH:17]([CH3:18])[CH2:16][CH3:15]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 5054ResorcinolHCID 6212ChloroformHCID 448893(S)-2-methylbutanoic acid

Product 1

HCID 147163011-(2,4-Dihydroxyphenyl)-2-methyl-1-butanoneYield 31.7%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
110 °C

Procedure

16.3 g of anhydrous zinc chloride was dissolved in 10.3 g of S-(+)-2-methylbutanoic acid by heating to 110° C. 13.2 g of resorcinol was added to the mixture and then the temperature of the admixture was raised to 150° C. over a period of 30 minutes under stirring. The reaction mixture was then cooled to the room temperature, and a mixture composed of 25 ml of hydrochloric acid and 25 ml of water was added thereto. The reaction mixture was then subjected to extraction for three times, each by using 50 ml of ethyl ether. The extracts were joined together and rinsed with an aquesous solution of NaHCO3 for three times, and then rinsed with water for three times. Anhydrous Na2SO4 was added to the rinsed extract to dry the ethyl ether extract. Ethyl ether was removed to obtain a liquid reaction product which was refined through silica gel column chromatography while using chloroform as the eluent. As a result, 6.2 g of 3-hydroxy-4 -(1-oxo-2-methylbutyl)phenol was obtained.

Workup

  1. temperaturethe temperature of the admixture was raised to 150° C. over a period of 30 minutes
  2. temperatureThe reaction mixture was then cooled to the room temperature
  3. additionwas added
  4. extractionThe reaction mixture was then subjected to extraction for three times
  5. washrinsed with an aquesous solution of NaHCO3 for three times
  6. washrinsed with water for three times
  7. additionAnhydrous Na2SO4 was added to the rinsed
  8. extractionextract
  9. dry with materialto dry the ethyl ether
  10. extractionextract
  11. customEthyl ether was removed
  12. customto obtain
  13. customa liquid reaction product which

Sources & evidence

ORD record
ord-c3a4b032dd93440ebe4df731949219df
Source dataset
uspto-grants-1991_10
Patent number
US05059345

Reaction notes

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