Ethylparaben → Ethyl 4-oxocyclohexanecarboxylate

HRID 2119109Notes

Reaction equation

HRID 2119109 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:4]([CH:5]1[CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]1)([O:3][CH2:1][CH3:2])=[O:12]

Participants

4

Reactant 2

HCID 8434EthylparabenHCID 178418361HCID 178418361, compound2×

Product 1

HCID 317638Ethyl 4-oxocyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Into a 1-liter magnetically stirred autoclave is placed 489 grams of ethyl-p-hydroxybenzoate having the structure: ##STR138## and 5% palladium on carbon catalyst (4 grams). The autoclave is sealed and hydrogenated at 125°-140° C. and 50 psig hydrogen pressure until the uptake of hydrogen is approximately 70% of theory. GLC analysis indicates that the reaction product at this point contains 71% ketone having the structure: ##STR139## 7.6% alcohol having the structure: ##STR140## and 20% starting material having the structure: ##STR141##

Workup

  1. customThe autoclave is sealed
  2. customhydrogenated at 125°-140° C.

Sources & evidence

ORD record
ord-7d2a825be53b4c36b7e6bdd3c0e3d055
Source dataset
uspto-grants-1987_07
Patent number
US04681976

Reaction notes

Loading…