Sulfuric Acid → Octanoic acid, 3,7-dimethyl-

HRID 2374124

Reaction equation

HRID 2374124 reaction equation
S(=O)(=O)(O)[OH:2].[CH3:6][CH:7]([CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:8][CH2:9][OH:10]>O.CC(C)=O.[O-2].[O-2].[O-2].[Cr+6]>[CH3:6][CH:7]([CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:8][C:9]([OH:2])=[O:10]

Participants

6

Conditions

Temperature
50 °C

Procedure

A solution of chromium trioxide (55.5 g, 0.555 mol) in water (68 ml) and 2M-sulphuric acid (12 ml) was added dropwise to a solution of 3,7-dimethyloctanol (43.7 g, 0.308 mol) in acetone (100 ml), the temperature was maintained at 40-60° C. and the reaction mixture was left stirring overnight. Acetone was carefully removed in vacuo, the reaction mixture was diluted in water and washed with diethyl ether (2×200 ml). The ethereal solution was washed with 10% sodium hydroxyde solution (200 ml); and the aqueous phase was acidified with 36% HCl (200 ml) and washed once more with diethyl ether (2×200 ml). The organic layer was dried (MgSO4) and the diethyl ether was removed in vacuo. The crude product was distilled to give a colourless oil.

Workup

  1. waitthe reaction mixture was left
  2. customAcetone was carefully removed in vacuo
  3. additionthe reaction mixture was diluted in water
  4. washwashed with diethyl ether (2×200 ml)
  5. washThe ethereal solution was washed with 10% sodium hydroxyde solution (200 ml)
  6. washwashed once more with diethyl ether (2×200 ml)
  7. dry with materialThe organic layer was dried (MgSO4)
  8. customthe diethyl ether was removed in vacuo
  9. distillationThe crude product was distilled
  10. customto give a colourless oil

Sources & evidence

ORD record
ord-4ec7e6322fd74f4780aa7c222c95e027
Source dataset
uspto-grants-2008_12
Patent number
US07462427B2

Linked notes

Loading…