2-Methyl-2-butene → 1-Methyl-4-(propan-2-yl)cyclohexane-1-carboxylic acid

HRID 389844Notes

Reaction equation

HRID 389844 reaction equation
[CH:1]([CH:4]1[CH2:9][CH2:8][C:7]([CH3:12])([CH:10]=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].CC(=CC)C.Cl([O-])=[O:19].[Na+].P([O-])(O)(O)=O.[Na+]>O.C(O)(C)(C)C>[CH:1]([CH:4]1[CH2:5][CH2:6][C:7]([CH3:12])([C:10]([OH:19])=[O:11])[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 461863041-Methyl-4-(propan-2-YL)cyclohexane-1-carbaldehyde

Product 1

HCID 133066451-Methyl-4-(propan-2-yl)cyclohexane-1-carboxylic acidYield 100.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A flask was charged with 10 g of 4-isopropyl-1-methyl cyclohexane carbaldehyde, 200 mL of tert-butanol and 100 mL of 2-methyl-2-butene. While stirring the contents of the flask, a solution prepared by dissolving 13 g of sodium chlorite and 11 g of sodium dihydrogenphosphate in 80 mL of water was added to the flask at 0° C. After stirring the contents of the flask at room temperature for 40 min, a part of tert-butanol in the flask was distilled off, and then a small amount of sulfuric acid was added to the flask. The resulting reaction mixture was extracted with an ether, and the thus obtained extract solution was concentrated and then purified by a silica gel column, thereby obtaining 11 g of 4-isopropyl-1-methyl cyclohexanecarboxylic acid.

Workup

  1. customa solution prepared
  2. additionwas added to the flask at 0° C
  3. stirringAfter stirring the contents of the flask at room temperature for 40 min
  4. distillationa part of tert-butanol in the flask was distilled off
  5. additiona small amount of sulfuric acid was added to the flask
  6. customThe resulting reaction mixture
  7. extractionwas extracted with an ether
  8. customthe thus obtained
  9. extractionextract solution
  10. concentrationwas concentrated
  11. custompurified by a silica gel column

Sources & evidence

ORD record
ord-4b1af3289f7b44baae2f2dd24442437d
Source dataset
uspto-grants-2013_02
Patent number
US08383574B2

Reaction notes

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