Water → HCID 15956913, compound

HRID 1501896Notes

Reaction equation

HRID 1501896 reaction equation
C[C:2]1([CH3:9])[O:6][C@H:5]([CH2:7][OH:8])[CH2:4][O:3]1.[OH-].[K+].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]CC.O>C1C=CC=CC=1>[CH2:2]([O:3][CH2:4][C@H:5]([CH2:7][OH:8])[OH:6])[CH2:9][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 81401-BromooctaneHCID 14797Potassium HydroxideHCID 736056(R)-Solketal

Product 1

HCID 15956913HCID 15956913, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

21 ml of (R)-(−)-2,2-dimethyl-1,3-dioxolane-4-methanol, 29 grams of powdered potassium hydroxide and 32 ml of 1-bromooctane were stirred in 150 ml benzene and refluxed for 6 hours, while removing the water formed by azeotropic distillation. The volume of the solvent was gradually reduced to about 100 ml. The reaction mixture was then cooled to room temperature and 200 ml water was added. The reaction mixture was then extracted thrice with 150 ml diethyl ether, the combined organic phase was washed with 100 ml water, and the solvent was then removed under reduced pressure. The obtained residue was dissolved in 100 ml of a 90:10:5 (v/v) mixture of methanol:water:concentrated hydrochloric acid, and the resulting solution was refluxed for 2 hours, followed by cooling to room temperature and addition of 100 ml water. The product was extracted thrice with 150 ml chloroform, washed consecutively with 150 ml water, 150 ml of saturated aqueous solution of sodium bicarbonate, and again with 100 ml water. The solvent was dried over anhydrous Na2SO4, filtered, and removed under reduced pressure, yielding 34 grams of (S)-1-octyl-glycerol.

Workup

  1. temperaturerefluxed for 6 hours
  2. customwhile removing the water
  3. customformed by azeotropic distillation
  4. extractionThe reaction mixture was then extracted thrice with 150 ml diethyl ether
  5. washthe combined organic phase was washed with 100 ml water
  6. customthe solvent was then removed under reduced pressure
  7. dissolutionThe obtained residue was dissolved in 100 ml of a 90:10:5 (v/v) mixture of methanol
  8. temperaturewater:concentrated hydrochloric acid, and the resulting solution was refluxed for 2 hours
  9. temperatureby cooling to room temperature
  10. additionaddition of 100 ml water
  11. extractionThe product was extracted thrice with 150 ml chloroform
  12. washwashed consecutively with 150 ml water, 150 ml of saturated aqueous solution of sodium bicarbonate
  13. dry with materialThe solvent was dried over anhydrous Na2SO4
  14. filtrationfiltered
  15. customremoved under reduced pressure

Sources & evidence

ORD record
ord-493793a66bc44ccba0c7c155415a368c
Source dataset
uspto-grants-2015_12
Patent number
US09206206B2

Reaction notes

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