Pyridine → 3,7-Dimethyl-7-ethoxyoctanal

HRID 918320Notes

Reaction equation

HRID 918320 reaction equation
[CH2:1]([O:3][C:4]([CH3:14])([CH3:13])[CH2:5][CH2:6][CH2:7][CH:8]([CH3:12])[CH2:9][CH2:10][OH:11])[CH3:2].N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>[O-2].[O-2].[O-2].[Cr+6].CCOCC>[CH2:1]([O:3][C:4]([CH3:13])([CH3:14])[CH2:5][CH2:6][CH2:7][CH:8]([CH3:12])[CH2:9][CH:10]=[O:11])[CH3:2]

Participants

6

Reactant 3

HCID 1049Pyridine2×HCID 516892Sodium BicarbonateHCID 227497647-Ethoxy-3,7-dimethyloctan-1-ol

Product 1

HCID 1607073,7-Dimethyl-7-ethoxyoctanal

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1.9 of 7-ethoxy-3,7-dimethyloctan-1-ol and 10 ml. of pyridine is added to a suspension of 8.0 g. of chromium trioxide in 100 ml. of pyridine with stirring under nitrogen. After about 4 hours at room temperature, the reaction is poured into saturated sodium bicarbonate and worked up with ether followed by washing with 2N NaOH, water, 10% HCl, water and brine and evaporated under reduced pressure to dryness and then filtered with hexane to yield 7-ethoxy-3,7-dimethyloctan-1-al.

Workup

  1. washby washing with 2N NaOH, water, 10% HCl, water and brine
  2. customevaporated under reduced pressure to dryness
  3. filtrationfiltered with hexane

Sources & evidence

ORD record
ord-7886681f04d644c79a96a3f5f0c211da
Source dataset
uspto-grants-1976_07
Patent number
US03970704

Reaction notes

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