Hydrochloric Acid → (3R)-3-benzoyloxy-tetradecanoyl chloride

HRID 1937069Notes

Reaction equation

HRID 1937069 reaction equation
[C:1]([O:9]C(=O)C1C=CC=CC=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:18].[OH:19][C@H:20]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:21][C:22]([OH:24])=O.[OH-].[Na+]>C1COCC1>[C:1]([O:19][C@H:20]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:21][C:22]([Cl:18])=[O:24])(=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7167Benzoic anhydrideHCID 14798Sodium HydroxideHCID 5288266(R)-3-hydroxytetradecanoic acid

Product 1

HCID 11303093(3R)-3-benzoyloxy-tetradecanoyl chlorideYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 20 L 3-neck round bottom flask equipped with a mechanical stirrer, nitrogen inlet, reflux condenser, heating mantle, vacuum system, and scrubber system for efficient removal of HCl and SO2 gases liberated during the reaction, is charged under nitrogen 15 moles of benzoic acid anhydride, 10 moles of concentrated anhydrous HCl in 4 L of THF, and 7.48 moles of the (3R)-3-hydroxy-tetradecanoic acid obtained from Example 1, above. The stirred mixture is placed under a N2 flow, which is vented to the scrubber system. The stirred mixture is heated to reflux for 3 hours during which the reaction becomes complete. The resulting solution is neutralized with 1N NaOH and the organic layer is separated from the aqueous layer. The aqueous layer is washed with THF and the resulting organic portions are combined, placed under vacuum and THF is removed. The resulting solid is dissolved in warm hexane, cooled and worked up to provide the product (3R)-3-benzoyloxy-tetradecanoyl chloride in about 95% yield.

Workup

  1. customTo a 20 L 3-neck round bottom flask equipped with a mechanical stirrer, nitrogen inlet
  2. temperaturereflux condenser
  3. temperatureheating mantle, vacuum system, and scrubber system
  4. customfor efficient removal of HCl and SO2 gases
  5. customliberated during the reaction
  6. temperatureThe stirred mixture is heated
  7. temperatureto reflux for 3 hours during which the reaction
  8. customthe organic layer is separated from the aqueous layer
  9. washThe aqueous layer is washed with THF
  10. customis removed
  11. dissolutionThe resulting solid is dissolved in warm hexane
  12. temperaturecooled

Sources & evidence

ORD record
ord-9a67740c14324d08a58b7b48a436bf6b
Source dataset
uspto-grants-2002_05
Patent number
US06392061B1

Reaction notes

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