Octanoic Acid → HCID 54500825, compound

HRID 1709722Notes

Reaction equation

HRID 1709722 reaction equation
[C:1]([OH:10])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(O)CCCCCO.[C:19]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]O)(=[O:27])[CH2:20][CH2:21]CCCCC>>[C:19]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:9][C:1](=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])(=[O:27])[CH:20]=[CH2:21]

Participants

4

Reactant 3

HCID 379Octanoic AcidHCID 123741,6-HexanediolHCID 23036666HCID 23036666, compound

Product 1

HCID 54500825HCID 54500825, compound

Procedure

A mixture of caprylic acid (110.5 g; 0.7662 mol) and 1,6-hexandiol (600 g; 5.077 mol) was heated to max. temperature 200° C. for 5 hours, while 25 g of organic volatile compounds and water was removed by distillation. The excess of 1,6-hexandiol was distilled off in vacuum and the residue was cooled and diluted with benzene (750 ml). The benzene solution was extracted with water (3×250 ml), the solvent was evaporated, and the product was distilled through a short empty column (100×25 mm). 6-Hydroxyhexyl caprylate (HHC) had b.p. 120° C./8 Pa. The main fraction containing 98.6% HHC was obtained in the yield of 157.2 g (84%). Elemental analysis for C14H28O3 theory: 68.81% C; 11.55% H; found: 68.65% C, 11.72% H. Infrared and 13C--NMR spectra proved the structure of HHC.

Workup

  1. temperaturewas heated to max
  2. customwhile 25 g of organic volatile compounds and water was removed by distillation
  3. distillationThe excess of 1,6-hexandiol was distilled off in vacuum
  4. temperaturethe residue was cooled
  5. additiondiluted with benzene (750 ml)
  6. extractionThe benzene solution was extracted with water (3×250 ml)
  7. customthe solvent was evaporated
  8. distillationthe product was distilled through a short empty column (100×25 mm)
  9. additionThe main fraction containing 98.6% HHC
  10. customwas obtained in the yield of 157.2 g (84%)

Sources & evidence

ORD record
ord-03f97dcaa43a424e832844d420b2d8c3
Source dataset
uspto-grants-1990_08
Patent number
US04950733

Reaction notes

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