Perchloric Acid → HCID 15332460, compound

HRID 487520Notes

Reaction equation

HRID 487520 reaction equation
[CH3:1][CH:2]([CH2:14][CH:15]([CH3:19])[CH2:16][CH2:17][CH3:18])[CH2:3][C:4](=[CH:11][O:12]C)[CH2:5][CH:6]([CH3:10])[C:7]([OH:9])=[O:8].Cl(O)(=O)(=O)=O>C(OCC)C>[CH3:1][CH:2]([CH2:14][CH:15]([CH3:19])[CH2:16][CH2:17][CH3:18])[CH2:3][CH:4]([CH:11]=[O:12])[CH2:5][CH:6]([CH3:10])[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 54542911HCID 54542911, compound

Product 1

HCID 15332460HCID 15332460, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To an ice-cold solution of 4-(2,4-dimethylheptanyl)-5-methoxy-2-methyl-4-pentenoic acid (11) (1.85 g, 6.85 mmol) in 95 ml diethyl ether in a 250 ml flask fitted with a magnetic stirrer and a dropping funnel, 25 ml of a 70 volume percent aqueous solution of perchloric acid was added slowly under a nitrogen atmosphere. After the addition was completed, the solution was stirred at room temperature for ten hours. The reaction mixture was poured into ice water, the organic layer separated, and the aqueous layer thoroughly extracted with three 100 ml portions of ether. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo to yield the aldehyde acid 4-(2,4-dimethylheptanyl)-2-methyl-5-oxo-pentanoic acid (12) as a yellow oil.

Workup

  1. additionAfter the addition
  2. customthe organic layer separated
  3. extractionthe aqueous layer thoroughly extracted with three 100 ml portions of ether
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-74f7a532b8284263a3b3761107581586
Source dataset
uspto-grants-1994_03
Patent number
US05296220

Reaction notes

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