Sulfuric Acid → 2-Cyclohexylpropanoic acid

HRID 728538Notes

Reaction equation

HRID 728538 reaction equation
[CH:1]1([CH:7]([CH3:12])[C:8]([O:10]C)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].S(=O)(=O)(O)O>>[CH:1]1([CH:7]([CH3:12])[C:8]([OH:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 12294713Methyl 2-cyclohexylpropanoate

Product 1

HCID 998162-Cyclohexylpropanoic acidYield 92.2%

Conditions

Temperature
80 °C

Procedure

Into a 500 ml round bottom flask 50 g of methyl 2-cyclohexylpropionate and 70 g of 25% sodium hydroxide were charged. The mixture was stirred at 80° C. for 8 hours. To the reaction mixture 120 g of 20% sulfuric acid was gradually added under ice-cooling to separate a carboxylic acid. The carboxylic acid was extracted with hexane. The mixture obtained was distilled to obtain 42.3 g of 2-cyclohexylpropionic acid having a civet- and animal-like odor (yield: 92%, purity: 99.9%).

Workup

  1. temperaturecooling
  2. customto separate a carboxylic acid
  3. extractionThe carboxylic acid was extracted with hexane
  4. customThe mixture obtained
  5. distillationwas distilled

Sources & evidence

ORD record
ord-664623ed94da4d669bf53e051125d8f4
Source dataset
uspto-grants-1991_09
Patent number
US05049544

Reaction notes

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