Acetone → Hexadecyl ethyleneglycol monoether

HRID 255962Notes

Reaction equation

HRID 255962 reaction equation
[CH2:1]([O:17][CH2:18][C:19](O)=[O:20])[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].B.CC(C)=O.O>O1CCCC1>[CH2:1]([O:17][CH2:18][CH2:19][OH:20])[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

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 6331BoraneHCID 13959070(Hexadecyloxy)acetic acid

Product 1

HCID 16492Hexadecyl ethyleneglycol monoetherYield 92.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 80 g of (hexadecyloxy) acetic acid in 350 ml of tetrahydrofuran was stirred at 0° C. while 798.71 ml of 1M borane in tetrahydrofuran was added dropwise over one hour. When addition was complete the mixture was stirred 2 hours than 50 ml of acetone was added followed by 60 ml of water dropwise. The tetrahydrofuran was allowed to evaporate overnight, then the residue was mixed with water and chloroform and heated to dissolve the solid. The organic layer was separated, dried and the solvent removed. The residue was recrystallized from cold methanol, giving 70.6 g of the desired compound as a white solid, mp 42°-44° C.

Workup

  1. additionwas added dropwise over one hour
  2. additionWhen addition
  3. additionwas added
  4. customto evaporate overnight
  5. additionthe residue was mixed with water and chloroform
  6. temperatureheated
  7. dissolutionto dissolve the solid
  8. customThe organic layer was separated
  9. customdried
  10. customthe solvent removed
  11. customThe residue was recrystallized from cold methanol

Sources & evidence

ORD record
ord-82f704fd68534a78bccb557fe2e82eb8
Source dataset
uspto-grants-1987_10
Patent number
US04699990

Reaction notes

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