p-Toluenesulfonic acid → HCID 13959073, compound

HRID 1199363Notes

Reaction equation

HRID 1199363 reaction equation
[CH2:1]([O:17][CH2:18][CH2:19][CH:20]1[CH2:22][O:21]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C1(C)C=CC(S(O)(=O)=[O:30])=CC=1>C(O)(=O)C>[CH2:1]([O:17][CH2:18][CH2:19][CH:20]([OH:30])[CH2:22][OH:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 139590722-[2-(Hexadecyloxy)ethyl]oxirane

Product 1

HCID 13959073HCID 13959073, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 40 g of [2-(hexadecyloxy)ethyl] oxirane in 270 ml of glacial acetic acid containing 0.265 g of p-toluenesulfonic acid was stirred at reflux for 4.5 hours. The acetic acid was removed, the residue dissolved in toluene the toluene removed and this residue dissolved in 300 ml of methanol. A solution of 17.9 g of sodium hydroxide in 18.5 ml of water was added, the mixture was stirred 1/2 hour and the solvent removed. The solid was dissolved in a mixture of ether and water. The ether layer was washed twice with saline, dried and filtered. The filtrate was warmed to dissolve the solid which formed, then concentrated to about 400 ml and allowed to stand at room temperature. Petroleum ether was added and the resulting solid collected, giving 32 g of the desired compound, mp 60°-61° C.

Workup

  1. temperatureat reflux for 4.5 hours
  2. customThe acetic acid was removed
  3. dissolutionthe residue dissolved in toluene the toluene
  4. customremoved
  5. dissolutionthis residue dissolved in 300 ml of methanol
  6. additionA solution of 17.9 g of sodium hydroxide in 18.5 ml of water was added
  7. customthe solvent removed
  8. dissolutionThe solid was dissolved in a mixture of ether and water
  9. washThe ether layer was washed twice with saline
  10. customdried
  11. filtrationfiltered
  12. temperatureThe filtrate was warmed
  13. dissolutionto dissolve the solid which
  14. customformed
  15. concentrationconcentrated to about 400 ml
  16. customto stand at room temperature
  17. additionPetroleum ether was added
  18. customthe resulting solid collected

Sources & evidence

ORD record
ord-005e1190bde24603b1c469cbf0b38bed
Source dataset
uspto-grants-1990_02
Patent number
US04900731

Reaction notes

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