Methanol → 16-Hydroxyhexadecanoic acid

HRID 325096Notes

Reaction equation

HRID 325096 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15].[OH-].[Na+].C(O)C[O:21][CH2:22][CH2:23]O.[CH3:26]O>>[OH:21][CH2:22][CH2:23][CH2:26][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15]

Participants

5

Reactant 4

HCID 887MethanolHCID 8117Diethylene GlycolHCID 14798Sodium HydroxideHCID 13906513-Hydroxytridecanoic acid

Product 1

HCID 1046616-Hydroxyhexadecanoic acidYield 81%

Conditions

Temperature
110 °C

Procedure

A compound of General formula 4 (n=10) (2.72 g, 10 mmole) was mixed with 2.0 g of ground sodium hydroxide, 16 ml of diethylene glycol, 1.3 ml of 85% hydrated hydrazine, and 0.6 ml of methanol, and stirred at 110° C. for 30 min. The mixture was heated up to 195-200° C. and stirred for 15 hours. Distillable components were completely distilled off to ensure its removal out of the system. The residue was cooled, acidified and subjected to extraction with chloroform. The chloroform layer was washed with water, and dried over anhydrous magnesium sulfate, and the solvent was distilled off to provide a crystalline material. It was recrystallized from benzene to produce 2.1 g of 15-hydroxypentadecanoic acid 2 (n=10). The yield was 81%. The product had a melting point of 84-86° C. The structure of 15-hydroxypentadecanoic acid was confirmed from IR and NMR spectral observation.

Workup

  1. temperatureThe mixture was heated up to 195-200° C.
  2. stirringstirred for 15 hours
  3. distillationDistillable components were completely distilled off
  4. customits removal out of the system
  5. temperatureThe residue was cooled
  6. extractionsubjected to extraction with chloroform
  7. washThe chloroform layer was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off
  10. customto provide a crystalline material
  11. customIt was recrystallized from benzene

Sources & evidence

ORD record
ord-a6017155ba1146f89aed4bd13a7e6bc1
Source dataset
uspto-grants-2001_04
Patent number
US06222049B1

Reaction notes

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