Hydrochloric Acid → (R)-3-hydroxytetradecanoic acid

HRID 1022294Notes

Reaction equation

HRID 1022294 reaction equation
O.[OH-].[Li+].[OH:4][C@H:5]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:6][C:7]([O:9]C)=[O:8].Cl>C1COCC1.O.C(OCC)C>[OH:4][C@H:5]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:6][C:7]([OH:9])=[O:8]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 98349453R-hydroxymyristic acid methyl ester

Product 1

HCID 5288266(R)-3-hydroxytetradecanoic acidYield 98.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (1.98 g, 47.2 mmol) was added to a solution of (R)-methyl 3-hydroxytetradecanoate (42, 8.17 g, 31.5 mmol) in THF (66 mL) and water (66 mL) and stirred at room temperature for 2 h. The mixture was then diluted with diethyl ether (1 L) and the pH adjusted to ˜3 with a solution of hydrochloric acid (1 N). The solution was then extracted with diethyl ether (200 mL), and the organic fractions were combined and dried over Na2SO4. Na2SO4 was removed by filtration and the filtrate was concentrated in vacuo to provide (R)-3-hydroxytetradecanoic acid (36, 7.59 g, 98%) as an off-white solid. 1H NMR (CDCl3) δ 3.99-3.94 (m, 1H), 2.45-2.39 (m, 2H), 1.47 (br s, 3H), 1.29 (br s, 17H), 0.89 (t, J=7.0 Hz, 3H).

Workup

  1. extractionThe solution was then extracted with diethyl ether (200 mL)
  2. dry with materialdried over Na2SO4
  3. customNa2SO4 was removed by filtration
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4be2f74794c748af84c8c13c42ec4f20
Source dataset
uspto-grants-2014_05
Patent number
US08722064B2

Reaction notes

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