Hydrochloric Acid → 2,5,8,11-Tetraoxatridecan-13-oic acid

HRID 1351024Notes

Reaction equation

HRID 1351024 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][C:13]([O:15]CC)=[O:14].[OH-].[Na+].Cl>[Cl-].[Na+].O>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20383039HCID 20383039, compound

Product 1

HCID 98593242,5,8,11-Tetraoxatridecan-13-oic acidYield 67.6%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

The product of step (a) (1.5 g) was stirred in a sodium hydroxide solution (0.1M, 30 mL) for 5 hours. The reaction mixture was adjusted to pH 2 by the addition of hydrochloric acid (2M) and then diluted with brine (300 mL). This was extracted with dichloromethane (2×300 mL) and the combined organic layers were dried and the solvent was removed in vacuo. Purification by chromatography on silica gel (Biotage), eluting with 10% methanol in dichloromethane gave the title compound as a clear oil (900 mg).

Workup

  1. extractionThis was extracted with dichloromethane (2×300 mL)
  2. customthe combined organic layers were dried
  3. customthe solvent was removed in vacuo
  4. customPurification by chromatography on silica gel (Biotage)
  5. washeluting with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-284f437507de41c6ba3e5b26617f9383
Source dataset
uspto-grants-2007_05
Patent number
US07217409B2

Reaction notes

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