2-Methyl-1-pentanol → HCID 118384826, compound

HRID 1778938Notes

Reaction equation

HRID 1778938 reaction equation
[C:1]([OH:22])(=[O: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][CH2:16][CH2:17][C:18]([OH:20])=[O:19].[CH3:23][CH:24]([CH2:27][CH2:28][CH3:29])[CH2:25]O>C1(C)C=CC=CC=1>[C:1]([O:22][CH2:23][CH:24]([CH3:25])[CH2:27][CH2:28][CH3:29])(=[O: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][CH2:16][CH2:17][C:18]([O:20][CH2:23][CH:24]([CH3:25])[CH2:27][CH2:28][CH3:29])=[O:19]

Participants

4

Reactant 2

HCID 77452-Methyl-1-pentanolHCID 70095Octadecanedioic acid3×

Product 1

HCID 118384826HCID 118384826, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
115 °C

Procedure

Octadecanedioic acid (ODDA, 5.00 g) was added to a 100-mL three-necked round-bottom flask. A Dean-Stark condenser was attached, followed by the addition of toluene to the ODDA and to the trap. 2-Methylpentyl alcohol (5.90 mL) was added to the ODDA mixture. The flask was immediately purged with nitrogen gas and p-toluenesulfonic acid (0.17 g) was added. The reaction mixture was heated to 115° C. and the reaction proceeded for 5 hours. Heat was then removed and the reaction mixture was allowed to cool to 60° C., at which point aqueous NaHCO3 (saturated) was added to achieve a neutral pH. After vigorous stirring, the organic layer was separated and dried over Na2SO4. The dried product was then subjected to a vacuum treatment to remove any residual solvent. A yellow oil was obtained. Analysis by 1H NMR provided the following chemical shifts: (400 MHz, CDCl3) δ 0.90-0.85 (m), 1.10-1.20 (m), 1.21-1.50 (m), 1.55-1.7 (t), 1.77 (o), 2.30 (t), 3.85 (dd), 3.95 (dd). Anaylsis by 13C NMR provided the following chemical shifts: (400 MHz, CDCl3) δ C, 173.947; CH, 32.366; CH2, 69.200, 35.691, 34.438, 29.701, 29.684, 29.641, 29.516, 29.319, 29.220, 25.095, 19.975; CH3, 16.885, 14.258.

Workup

  1. customThe flask was immediately purged with nitrogen gas and p-toluenesulfonic acid (0.17 g)
  2. additionwas added
  3. temperatureHeat
  4. customwas then removed
  5. temperatureto cool to 60° C., at which point aqueous NaHCO3 (saturated)
  6. additionwas added
  7. customAfter vigorous stirring, the organic layer was separated
  8. dry with materialdried over Na2SO4
  9. customto remove any residual solvent
  10. customA yellow oil was obtained
  11. customAnalysis by 1H NMR provided the following chemical shifts
  12. customAnaylsis by 13C NMR provided the following chemical shifts

Sources & evidence

ORD record
ord-f67e5e3506554589a0c54cf43fc2063a
Source dataset
uspto-grants-2016_02
Patent number
US09267013B2

Reaction notes

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