Hydrochloric Acid → Octanal, 6-methoxy-2,6-dimethyl-

HRID 1710324Notes

Reaction equation

HRID 1710324 reaction equation
[OH-].[K+].COC([CH:7]1[C:9]([CH2:11][CH2:12][CH2:13][C:14]([O:18][CH3:19])([CH3:17])[CH2:15][CH3:16])([CH3:10])[O:8]1)=O.Cl.P(=O)(O)(O)O>O>[CH3:19][O:18][C:14]([CH3:17])([CH2:15][CH3:16])[CH2:13][CH2:12][CH2:11][CH:9]([CH3:10])[CH:7]=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1004Phosphoric AcidHCID 14797Potassium Hydroxide2×HCID 86623835HCID 86623835, compound

Product 1

HCID 24755581Octanal, 6-methoxy-2,6-dimethyl-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

180 g Potassium hydroxide dissolved in 800 ml water was added over 2 h to 810 g 3-(4-methoxy-4-methyl-hexyl)-3-methyl-oxirane-2-carboxylic acid methyl ester at a temperature of 0° C. to 5° C. Then 36 g KOH dissolved in 150 ml water was added in portions till the colour change from orange to beige persisted. The mixture which had pH 11 was then acidified at 0° C. by the addition of HCl 32% (300 ml, added over 30 minutes), followed by diluted phosphoric acid till pH 3 was reached. The phases were separated and the aqueous phase extracted with tert.-butyl methyl ether. The combined organic phases were washed with concentrated NaCl solution prior to evaporating the solvent. The very viscous oil which remained (780 g) was added dropwise over a period of 3 h to 300 ml PEG 200 which was kept at 160° C. Thereby the product distilled off. After the addition, steam was injected for about 30 minutes to distil off any steam-volatile product. The two phases of the distillate were separated and the aqueous phase extracted with tert.-butyl methyl ether. The combined organic phases were washed with KHCO3 and NaCl. Evaporation of the solvent afforded 380 g of a faintly yellow oil which was distilled over a 60 cm Sulzer column to give 338 g 6-methoxy-2,6-dimethyl-octanal (bp. 65°-66° C./0.3 Torr=0.399 mbar).

Workup

  1. additionwas added in portions till the colour change from orange
  2. customThe phases were separated
  3. extractionthe aqueous phase extracted with tert.-butyl methyl ether
  4. washThe combined organic phases were washed with concentrated NaCl solution
  5. customto evaporating the solvent
  6. additionwas added dropwise over a period of 3 h to 300 ml PEG 200 which
  7. customwas kept at 160° C
  8. distillationThereby the product distilled off
  9. additionAfter the addition, steam
  10. customto distil off any steam-volatile product
  11. customThe two phases of the distillate were separated
  12. extractionthe aqueous phase extracted with tert.-butyl methyl ether
  13. washThe combined organic phases were washed with KHCO3 and NaCl
  14. customEvaporation of the solvent
  15. customafforded 380 g of a faintly yellow oil which
  16. distillationwas distilled over a 60 cm Sulzer column

Sources & evidence

ORD record
ord-6956d6fc810d480098c706a0fa4e73e8
Source dataset
uspto-grants-2010_09
Patent number
US07790668B2

Reaction notes

Loading…