Eicosanedioic Acid → 1,20-Eicosanediol

HRID 217091

Reaction equation

HRID 217091 reaction equation
[C:1](O)(=[O:23])[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][CH2:16][CH2:17][CH2:18][CH2:19][C:20](O)=[O:21].C1COCC1.O.C([O-])(O)=O.[Na+]>O>[CH2:20]([OH:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:23]

Participants

5

Reactant 3

HCID 75502Eicosanedioic AcidHCID 516892Sodium BicarbonateHCID 21881883Oxolane--water (1/1)

Product 1

HCID 41346901,20-Eicosanediol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Icosane-1,20-diol was synthesized according to Yoon et al., J. Org. Chem. 1973, 38(16), 2786-2792. Briefly, under N2 atmosphere to 25 g eicosanedioic acid 100 ml THF was added. Then 474.5 ml of borane/THF complex was added dropwise over 1.5 hours. The mixture was refluxed over night before 200 ml THF/H2O 1:1 were added dropwise. Under further stirring 100 g NaHCO3 dissolved in 250 ml H2O was added and two hours later 1000 ml H2O was added to the mixture and the precipitate was removed by filtration. At the next day and the day after next a white precipitate was removed by filtration from the mixture, dried and recrystallized from acetic acid ethyl ester. The product was characterized by thin layer chromatography and 1H-NMR.

Workup

  1. additionThen 474.5 ml of borane/THF complex was added dropwise over 1.5 hours
  2. additionwere added dropwise
  3. additionwas added to the mixture
  4. customthe precipitate was removed by filtration
  5. customAt the next day and the day after next a white precipitate was removed by filtration from the mixture
  6. customdried
  7. customrecrystallized from acetic acid ethyl ester

Sources & evidence

ORD record
ord-2d7e4e3913bc4226b406c3e8f5d0e884
Source dataset
uspto-grants-2012_06
Patent number
US08193246B2

Linked notes

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