Sulfuric Acid → Tert-butyl 2-cyclohexylpropionate

HRID 728541Notes

Reaction equation

HRID 728541 reaction equation
[CH:1]1([CH:7]([CH3:11])[C:8]([OH:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:12]=[C:13]([CH3:15])[CH3:14].S(=O)(=O)(O)O>CCOCC>[CH:1]1([CH:7]([CH3:11])[C:8]([O:10][C:13]([CH3:15])([CH3:14])[CH3:12])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 998162-Cyclohexylpropionic acid

Product 1

HCID 13087925Tert-butyl 2-cyclohexylpropionateYield 11%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Into a 500 ml round bottom flask 30 g of 2-cyclohexylpropionic acid and 200 ml of ether were charged and cooled to 0° C. After 100 g of isobutene gas was introduced, 0.5 g of sulfuric acid was charged into the mixture, the mixture was then stirred at 0° C. for 40 hours. The reaction mixture was washed with water and distilled under reduced pressure to obtain 4.5 g of tert-butyl 2-cyclohexylpropionate having a woody and floral odor (yield: 11%, purity: 98.7%).

Workup

  1. washThe reaction mixture was washed with water
  2. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-21dea613756f41dd98676c13f2bb475e
Source dataset
uspto-grants-1991_09
Patent number
US05049544

Reaction notes

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