Sulfuric Acid → Cyclohexaneacetic acid, 3,3,5-trimethyl-

HRID 1461954Notes

Reaction equation

HRID 1461954 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:7][CH:6]([CH3:8])[CH2:5][CH:4]([CH2:9][C:10]([O:12]CC)=[O:11])[CH2:3]1.[OH-].[Na+].S(=O)(=O)(O)O>O>[CH3:15][C:2]1([CH3:1])[CH2:7][CH:6]([CH3:8])[CH2:5][CH:4]([CH2:9][C:10]([OH:12])=[O:11])[CH2:3]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 122545Ethyl (3,3,5-trimethylcyclohexyl)acetate

Product 1

HCID 102954Cyclohexaneacetic acid, 3,3,5-trimethyl-Yield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

875 g of ethyl 3,3,5-trimethyl-cyclohexylacetate are treated in 2.2 l of water with 670 g of 30% sodium hydroxide and the mixture is held at reflux temperature for 21/2 hours while stirring. After cooling, the mixture is neutralized, acidified with 420 g of 63% sulphuric acid and extracted with cyclohexane. The cyclohexane extract is washed neutral, evaporated and the 770 g of crude product are distilled. There are obtained 630 g of 3,3,5-trimethyl-cyclohexylacetic acid. (Yield: 82%).

Workup

  1. temperatureat reflux temperature for 21/2 hours
  2. temperatureAfter cooling
  3. extractionextracted with cyclohexane
  4. extractionThe cyclohexane extract
  5. washis washed neutral
  6. customevaporated
  7. distillationthe 770 g of crude product are distilled

Sources & evidence

ORD record
ord-7d55fbf5e5534c99b9480ca9485b6e28
Source dataset
uspto-grants-1984_07
Patent number
US04457862

Reaction notes

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