Ethylparaben → Ethyl 4-hydroxycyclohexanecarboxylate

HRID 1285111Notes

Reaction equation

HRID 1285111 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[H][H]>[Ni].C(O)C>[CH2:9]([O:8][C:6]([CH:5]1[CH2:11][CH2:12][CH:2]([OH:1])[CH2:3][CH2:4]1)=[O:7])[CH3:10]

Participants

5

Reactant 2

HCID 8434EthylparabenHCID 178418361HCID 178418361, compound2×

Product 1

HCID 86973Ethyl 4-hydroxycyclohexanecarboxylateYield 79.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

In an autoclave made of stainless steel having a volume of 1 liter were placed 142 g (0.86 mole) of ethyl para-hydroxybenzoate, 10 g of Raney Ni catalyst (activity W-7) and 400 ml of ethanol, and reacted with stirring at a pressure of hydrogen of 100 kg/cm2 and a reaction temperature of 150° C. for 20 hours. After the autoclave was allowed to cool to room temperature, the hydrogen in the vessel was released, and the Raney Ni catalyst was then removed by suction filtration. The filtrate was concentrated by means of a rotary evaporator and then distilled under reduced pressure to obtain 117 g (0.68 mole, yield 79%) of 4-ethoxycarbonylcyclohexanol having a boiling point of 98° to 104° C./4 mmHg.

Workup

  1. customreacted
  2. customthe Raney Ni catalyst was then removed by suction filtration
  3. concentrationThe filtrate was concentrated by means of a rotary evaporator
  4. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-b6f59fd6add9426b8503fc9748f9f537
Source dataset
uspto-grants-1986_01
Patent number
US04565767

Reaction notes

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