Water → HCID 86657042, compound

HRID 1501906Notes

Reaction equation

HRID 1501906 reaction equation
C[C:2]1([CH3:9])[O:6][C@H:5]([CH2:7][OH:8])[CH2:4][O:3]1.[OH-].[K+].[CH2:12]([CH2:28]S([O-])(=O)=O)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24]CCC.O>C1C=CC=CC=1>[CH2:2]([O:3][CH2:4][C@H:5]([CH2:7][OH:8])[OH:6])[CH2:9][CH2:28][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 736056(R)-SolketalHCID 86657043HCID 86657043, compound

Product 1

HCID 86657042HCID 86657042, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5.32 grams of (R)-(−)-2,2-dimethyl-1,3-dioxolane-4-methanol, 12.26 grams of powdered potassium hydroxide and 10 grams of cis-9-hexadecenyl-methanesulfonate were stirred in 250 ml benzene and refluxed for 10.5 hours, while removing the water formed by azeotropic distillation. The volume of the solvent was gradually reduced to about 50 ml. The reaction mixture was cooled to room temperature, 50 ml water was added, and the mixture was extracted thrice with 100 ml diethyl ether. The combined organic phase was washed with 100 ml water and the solvent was removed under reduced pressure. The residue (12.01 grams) was dissolved in 200 ml of a 90:10:3 (v/v) mixture of methanol:water:concentrated hydrochloric acid, and the resulting solution was stirred at room temperature overnight and then refluxed for 1 hour. After cooling to room temperature, 100 ml water was added. The product was extracted thrice with 75 ml diethyl ether, washed consecutively with 100 ml water, 100 ml saturated aqueous solution of sodium bicarbonate, and again with 100 ml water. After drying on Na2SO4, the solvent was removed under reduced pressure, yielding 9.104 grams of crude 1-(cis-9-hexadecenyl)-sn-glycerol. The crude product was purified by chromatography on a silica gel (30 grams) column. 9.07 grams of pure 1-(cis-9-hexadecenyl)-glycerol was eluted by chloroform followed by a mixture of chloroform and 5% methanol. The yield was 91.8%.

Workup

  1. temperaturerefluxed for 10.5 hours
  2. customwhile removing the water
  3. customformed by azeotropic distillation
  4. extractionthe mixture was extracted thrice with 100 ml diethyl ether
  5. washThe combined organic phase was washed with 100 ml water
  6. customthe solvent was removed under reduced pressure
  7. dissolutionThe residue (12.01 grams) was dissolved in 200 ml of a 90:10:3 (v/v) mixture of methanol
  8. temperaturerefluxed for 1 hour
  9. temperatureAfter cooling to room temperature
  10. addition100 ml water was added
  11. extractionThe product was extracted thrice with 75 ml diethyl ether
  12. washwashed consecutively with 100 ml water, 100 ml saturated aqueous solution of sodium bicarbonate
  13. customAfter drying on Na2SO4
  14. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7e963f54c31042daab6bb03fa01e83e0
Source dataset
uspto-grants-2015_12
Patent number
US09206206B2

Reaction notes

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