Hydrochloric Acid → HCID 59204987, compound

HRID 2241914Notes

Reaction equation

HRID 2241914 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:12]=[C:8]([C:9]([OH:11])=[O:10])[C:7]([OH:13])=[CH:6][CH:5]=1.[CH3:14][O:15][CH2:16][CH2:17][O:18][CH2:19]Cl.Cl>O1CCCC1.O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([O:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 94475-Chlorosalicylic AcidHCID 14798Sodium Hydroxide2×HCID 775901-(Chloromethoxy)-2-methoxyethane

Product 1

HCID 59204987HCID 59204987, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide (7.20 g, 180 mmol) was added to a solution of 5-chlorosalicylic acid (10.36 g, 60 mmol) in tetrahydrofuran (60 ml). (2-Methoxyethoxy)methyl chloride (15.1 ml, 132 mmol) was added to the mixture, and the mixture was stirred for 18 hours. 2N Aqueous sodium hydroxide (80 ml) was added to the reaction mixture, and the mixture was refluxed for 2 hours. The water layer was adjusted to pH=3 by addition of 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane ethyl acetate=1:1) to give the title compound (12.8 g, 82%) as a colorless liquid.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe residue obtained by evaporation of the solvent under reduced pressure
  6. customwas purified by column chromatography on silica gel (n-hexane ethyl acetate=1:1)

Sources & evidence

ORD record
ord-8c3979a32024453a82ce1b4584a2cf1a
Source dataset
uspto-grants-2010_03
Patent number
US07671058B2

Reaction notes

Loading…