Hydrochloric Acid → HCID 19004309, compound

HRID 2225698

Reaction equation

HRID 2225698 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[OH-].[Na+].S([O-])(=O)(=O)C.Cl.[CH3:21][O:22][CH2:23][CH2:24]O>CS(C)=O>[CH3:21][O:22][CH2:23][CH2:24][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:12])[C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3554-HydroxyphenylglyoxylateHCID 80192-MethoxyethanolHCID 14798Sodium HydroxideHCID 85257Methanesulfonate

Product 1

HCID 19004309HCID 19004309, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid (0.498 g) in dimethylsulfoxide (5 mL) under argon was treated with 4N sodium hydroxide (1.5 mL), stirred for 5 minutes and treated with the mesylate prepared from 2-methoxyethanol (0.462 g) . The mixture was heated at 60° C. for 3 hours and poured into excess 1N hydrochloric acid. The product was extracted into diethyl ether (3×50 mL) and the organic layers were washed in turn with water (2×25 mL). The combined organic layers were dried (Na2SO4), filtered, and evaporated to give 0.56 g of crude product as a solid. Crystallization from ethyl acetate-hexane provided 0.3 g of 4-[[2-(methoxy)ethyl]oxy]-alphaoxobenzeneacetic acid, mp 129°-130° C.

Workup

  1. extractionThe product was extracted into diethyl ether (3×50 mL)
  2. washthe organic layers were washed in turn with water (2×25 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto give 0.56 g of crude product as a solid
  7. customCrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-14f8fd80fc5047689740c8e8375a53e9
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Linked notes

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