1-Octanol → HCID 23193717, compound

HRID 728687Notes

Reaction equation

HRID 728687 reaction equation
C1[O:6][C:5]([CH2:11][C:12]([OH:14])=[O:13])([CH2:7][C:8]([OH:10])=[O:9])[C:3](=[O:4])[O:2]1.C(N(CC)CC)C.[CH2:22](O)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>C(O)C>[CH2:22]([CH:7]([C:5]([CH2:11][C:12]([OH:14])=[O:13])([C:3]([OH:2])=[O:4])[OH:6])[C:8]([OH:10])=[O:9])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 9571-OctanolHCID 8471TriethylamineHCID 8945Anhydromethylenecitric acid

Product 1

HCID 23193717HCID 23193717, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2 (50.0 g, 0.245 mole), in ethanol-free chloroform (500 ml), was added triethylamine (75 ml, 0.538 mole) followed by octanol (80 ml. 0.508 mole). The resulting solution was refluxed for 45 hours, cooled and the chloroform removed by evaporation at 40° C. The residue was dissolved in ethyl acetate (400 ml) and this solution washed 3 times with cold saturated sodium bicarbonate solution (200 ml). The combined bicarbonate extract was washed twice with ethyl acetate (200 ml). The bicarbonate extract was then adjusted to pH 2 by the drop wise addition of concentrated HCl (≈78 ml). The cloudy solution was extracted with three portions of ethyl acetate (200 ml), the combined ethyl acetate extract dried (magnesium sulfate), filtered and evaporated, finally in high vacuum at 50° C. to give 3a (61.7 g, 90%) as an oil. The oil was dissolved in 200 ml of hot toluene on the steam bath and filtered from some insoluble material. The filtrate was kept at room temperature overnight, then, the crystals were collected, washed with toluene and dried to give 3a (43.09 g, 58%), mp 65.8°-66.7° C.

Workup

  1. temperatureThe resulting solution was refluxed for 45 hours
  2. temperaturecooled
  3. customthe chloroform removed by evaporation at 40° C
  4. dissolutionThe residue was dissolved in ethyl acetate (400 ml)
  5. washthis solution washed 3 times with cold saturated sodium bicarbonate solution (200 ml)
  6. extractionThe combined bicarbonate extract
  7. washwas washed twice with ethyl acetate (200 ml)
  8. extractionThe bicarbonate extract
  9. additionwas then adjusted to pH 2 by the drop wise addition of concentrated HCl (≈78 ml)
  10. extractionThe cloudy solution was extracted with three portions of ethyl acetate (200 ml)
  11. extractionthe combined ethyl acetate extract
  12. dry with materialdried (magnesium sulfate)
  13. filtrationfiltered
  14. customevaporated, finally in high vacuum at 50° C.

Sources & evidence

ORD record
ord-8286c10b6ece49af80fa4d77e05ccef0
Source dataset
uspto-grants-1991_09
Patent number
US05049699

Reaction notes

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