p-Toluenesulfonic acid → 3-Hexadecyloxybutane-1,2-diol

HRID 1761729Notes

Reaction equation

HRID 1761729 reaction equation
[CH2:1]([O:17][CH:18]([CH:20]1[CH2:22][O:21]1)[CH3:19])[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][CH:18]([CH3:19])[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 14500858[1-(Hexadecyloxy)ethyl]oxirane

Product 1

HCID 142331613-Hexadecyloxybutane-1,2-diolYield 7,520.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 30 g of [1-(hexadecyloxy)ethyl]oxirane, 0.2 g of p-toluenesulfonic acid and 200 ml of glacial acetic acid was refluxed for 4.5 hours, then the acetic acid was removed. Toluene was added and removed. The residue was dissolved in 225 ml of methanol and 13.44 g of sodium hydroxide in 14 ml of water was added. This mixture was stirred 1/2 hour, the solvent removed and the residue extracted twice with ether. The ether extracts were combined, washed with brine, dried and the solvent removed. The resulting oil was diluted via a Kugelrohr (200° C., 0.5 mm), giving 28.87 g of the desired compound as a white sticky solid.

Workup

  1. temperaturewas refluxed for 4.5 hours
  2. customthe acetic acid was removed
  3. additionToluene was added
  4. customremoved
  5. dissolutionThe residue was dissolved in 225 ml of methanol
  6. addition13.44 g of sodium hydroxide in 14 ml of water was added
  7. customthe solvent removed
  8. extractionthe residue extracted twice with ether
  9. washwashed with brine
  10. customdried
  11. customthe solvent removed
  12. additionThe resulting oil was diluted via a Kugelrohr (200° C., 0.5 mm)

Sources & evidence

ORD record
ord-6bf36c30899a49c49312947a831ab152
Source dataset
uspto-grants-1989_05
Patent number
US04827011

Reaction notes

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