Ethylparaben → HCID 13782250, compound

HRID 484956Notes

Reaction equation

HRID 484956 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[CH3:2].[H][H]>[Pd].C(O)(C)C>[C:4]([O:11][CH:8]1[CH2:9][CH2:10][CH:5]([C:4]([O:3][CH2:1][CH3:2])=[O:12])[CH2:6][CH2:7]1)(=[O:3])[CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 8434EthylparabenHCID 178418361HCID 178418361, compound

Product 1

HCID 13782250HCID 13782250, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

289 Grams of ethyl-p-hydroxybenzoate and 4 grams of 5% palladium on carbon are charged to a 1-liter magnetically stirred autoclave. The material is hydrogenated at 125°-140° C. and 50 psig hydrogen pressure. Hydrogenation is continued until the uptake is approximately 70% of theory. GLC analysis indicates that the reaction mass is now 71% ketone and 7.6% alcohol. The reaction product is cooled, diluted with isopropyl alcohol, filters. The isopropyl alcohol is removed by stripping and the remainder is distilled through a short column. 286 Grams of the resulting distillate is admixed with 75 grams of propionicanhydride at 100° C. for a period of four hours. The resulting material is washed until neutral and distilled through an eight plate vigreux column yielding the following fractions:

Workup

  1. customis hydrogenated at 125°-140° C.
  2. temperatureThe reaction product is cooled
  3. customThe isopropyl alcohol is removed
  4. distillationthe remainder is distilled through a short column
  5. washThe resulting material is washed until neutral and
  6. distillationdistilled through an eight plate vigreux column
  7. customyielding the following fractions

Sources & evidence

ORD record
ord-cefb397157fb45cab377e23e0530abc5
Source dataset
uspto-grants-1985_08
Patent number
US04534890

Reaction notes

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