1,3-Propanediol → 1,3-Di-(z-15-tetracosenoyloxy)propane

HRID 432975Notes

Reaction equation

HRID 432975 reaction equation
[C:1]([OH:26])(=[O:25])[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]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[CH2:27](O)[CH2:28][CH2:29][OH:30].[PH2](O)=O>>[C:1]([O:26][CH2:3][CH2:2][CH2:1][O:25][C:29](=[O:30])[CH2:28][CH2:27][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]/[CH:13]=[CH:12]\[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH3:4])(=[O:25])[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]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 3

HCID 104421,3-PropanediolHCID 4124402Phosphinic AcidHCID 5281120Nervonic Acid

Product 1

HCID 98755151,3-Di-(z-15-tetracosenoyloxy)propane

Conditions

Temperature
160 °C

Procedure

z-15-Tetracosenoic acid (available from Sigma Chemicals), (0.286 mol, 104.7 g), propane-1,3-diol (0.136, 10.3 g) and hypophosphorous acid (0.4 g) was heated with stirring to 160° C. under nitrogen. After 6 h, TLC (80:18:2 petroleum ether-ethyl ether-acetic acid) indicated that the reaction had gone to completion (Rf: 0.63). The mixture was cooled down to room temperature and petroleum ether (1500 mL) was added. The resulting solution was washed with saturated sodium bicarbonate (3×150 mL) and saturated sodium chloride (3×150 mL). It was then dried over anhydrous sodium sulphate and concentrated to dryness. Residual mono-ester and fatty acid were removed by distillation in vacuo (230° C., 10−2 mbar). The resulting oil was dissolved into petroleum ether to make up a 33% solution and was passed down a silica column. Hexane was finally removed to yield 1,3-di-(z-15-tetracosenoyloxy)propane as a colourless oil.

Workup

  1. temperatureThe mixture was cooled down to room temperature
  2. washThe resulting solution was washed with saturated sodium bicarbonate (3×150 mL) and saturated sodium chloride (3×150 mL)
  3. dry with materialIt was then dried over anhydrous sodium sulphate
  4. concentrationconcentrated to dryness
  5. customResidual mono-ester and fatty acid were removed by distillation in vacuo (230° C., 10−2 mbar)
  6. dissolutionThe resulting oil was dissolved into petroleum ether
  7. customHexane was finally removed

Sources & evidence

ORD record
ord-bfe7a1c9907e4f9bafc1b8d141d9d841
Source dataset
uspto-grants-2003_12
Patent number
US06664406B1

Reaction notes

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