Hydrochloric Acid → 12-(3-Chloro-5-formyl-2,6-dihydroxy-4-methylphenyl)dodecanoic acid

HRID 59631Notes

Reaction equation

HRID 59631 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:5]([OH:30])=[C:6]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27]CC)=[O:26])[C:7]([OH:13])=[C:8]([CH:11]=[O:12])[C:9]=1[CH3:10].Cl.[Na+].[Cl-]>CC(C)=O.CCOC(C)=O.O>[Cl:3][C:4]1[C:5]([OH:30])=[C:6]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])[C:7]([OH:13])=[C:8]([CH:11]=[O:12])[C:9]=1[CH3:10]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 87428760Ethyl 12-(3-chloro-5-formyl-2,6-dihydroxy-4-methylphenyl)dodecanate

Product 1

HCID 8742887312-(3-Chloro-5-formyl-2,6-dihydroxy-4-methylphenyl)dodecanoic acid

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

NaOH (21 mg, 0.48 mmol) was added to a mixed solution of 215-15-COOEt (101 mg, 0.246 mmol) in acetone (1.3 ml)/H2O (0.7 ml) at room temperature followed by stirring for 12 hours. After dilution of the reaction solution with EtOAc, the diluted solution was acidified with a 1 M aqueous HCl solution. After addition of a saturated aqueous NaCl solution, the organic layer was separated. The aqueous layer was then extracted with EtOAc twice, and the combined organic layer was dried over Na2SO4. After evaporation of the solvent, the residue was purified by column chromatography on silica gel (Hexane:EtOAc=2:1) to yield the target product.

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was then extracted with EtOAc twice
  3. dry with materialthe combined organic layer was dried over Na2SO4
  4. customAfter evaporation of the solvent
  5. customthe residue was purified by column chromatography on silica gel (Hexane:EtOAc=2:1)
  6. customto yield the target product

Sources & evidence

ORD record
ord-cb01281cf78a4835bda1ca8a36e8c9da
Source dataset
uspto-grants-2016_09
Patent number
US09440913B2

Reaction notes

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