Hydrochloric Acid → 3-Hydroxy-4-(1-oxo-2-phenylpropyl)phenol

HRID 345744Notes

Reaction equation

HRID 345744 reaction equation
[CH3:1][C@H:2]([C:9]([OH:11])=O)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:12]1([CH:19]=[CH:18][CH:17]=[C:15]([OH:16])[CH:14]=1)[OH:13].Cl.O>[Cl-].[Zn+2].[Cl-].C(Cl)(Cl)Cl>[OH:13][C:12]1[CH:14]=[C:15]([OH:16])[CH:17]=[CH:18][C:19]=1[C:9](=[O:11])[CH:2]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 5054ResorcinolHCID 27246222-Phenylpropionic acid, (+)-

Product 1

HCID 107765403-Hydroxy-4-(1-oxo-2-phenylpropyl)phenolYield 41.3%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
110 °C

Procedure

3.0 g (20 millimols) of S-(+)-2-phenylpropionic acid was mixed with 3.3 g (24 millimols) of anhydrous zinc chloride and heated to 110° C. to dissolve the latter in the former. 2.64 g (24 millimols) of resorcinol was added to the solution and further heated to 150° C. over a period of 20 minutes while stirring the reaction mixture. The reaction mixture was then cooled to the room temperature. 10 ml of concentrated hydrochloric acid solution and 50 ml of water was added to the reaction mixture, and the reaction product was extracted for 3 times while using 50 ml of ethyl ether in each extraction operation. The extract in ethyl ether was rinsed with an aqueous solution of NaHCO3 for two times, and then rinsed with water for three times. The extract in ethyl ether was then dried by adding anhydrous Na2SO4. The drying agent was removed by filtration and ethyl ether was removed by distillation to obtain 3.6 g of a crude product. The crude product was refined through silica gel column chromatography while using chloroform as the eluent. As a result, 2.0 g of 3-hydroxy-4-(1-oxo-2-phenylpropyl)phenol was obtained.

Workup

  1. dissolutionto dissolve the latter in the former
  2. temperaturefurther heated to 150° C. over a period of 20 minutes
  3. temperatureThe reaction mixture was then cooled to the room temperature
  4. extractionthe reaction product was extracted for 3 times
  5. extractionThe extract in ethyl ether
  6. washwas rinsed with an aqueous solution of NaHCO3 for two times
  7. washrinsed with water for three times
  8. extractionThe extract in ethyl ether
  9. customwas then dried
  10. additionby adding anhydrous Na2SO4
  11. customThe drying agent was removed by filtration and ethyl ether
  12. customwas removed by distillation
  13. customto obtain 3.6 g of a crude product

Sources & evidence

ORD record
ord-8439b5efddb24e01890326a157eedaa3
Source dataset
uspto-grants-1991_10
Patent number
US05059345

Reaction notes

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