Sulfuric Acid → 3,7-Dimethyloct-3-enoic acid

HRID 392843Notes

Reaction equation

HRID 392843 reaction equation
S(=O)(=O)(O)[OH:2].[CH3:6]/[C:7](=[CH:11]\[CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])/[CH2:8][CH2:9][OH:10]>O.CC(C)=O.O.O.O.[Cr]>[CH3:6][C:7](=[CH:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:8][C:9]([OH:2])=[O:10]

Participants

6

Reactant 2

HCID 1118Sulfuric AcidHCID 22661166HCID 22661166, compound

Product 1

HCID 713655083,7-Dimethyloct-3-enoic acid

Reagents, catalysts & solvents 3

HCID 1478712182-82-0CatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 8.84 g (88.4 mmol, 3 eq) of chromium VI oxide in 25 mL of water in the presence of 8.2 mL of 95% sulphuric acid is added to a solution of 4.6 g (29.5 mmol, 1 eq) of (E)-3,7-dimethyloct-3-enol in 250 mL of acetone, at 0° C., while maintaining the temperature at 0° C. After addition, the reaction mixture is stirred for 15 minutes at 0° C. and the reaction is then quenched by adding 250 mL of water. The reaction medium is extracted with 2×250 mL of diethyl ether. The organic phases are combined, washed with saturated sodium chloride solution and dried over anhydrous sodium sulphate, and the residue is then filtered through silica gel: eluent (95/5→75/25 Cy/EtOAc).

Workup

  1. additionAfter addition
  2. customthe reaction is then quenched
  3. additionby adding 250 mL of water
  4. extractionThe reaction medium is extracted with 2×250 mL of diethyl ether
  5. washwashed with saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationthe residue is then filtered through silica gel

Sources & evidence

ORD record
ord-c8de4d884ec946e2a73d0ce20047b62b
Source dataset
uspto-grants-2004_10
Patent number
US06803382B2

Reaction notes

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