Hydrochloric Acid → HCID 19004267, compound

HRID 2225687Notes

Reaction equation

HRID 2225687 reaction equation
[Na+].[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:26])[C:23]([O-:25])=[O:24])=[CH:18][CH:17]=1.Cl>ClCCl>[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:26])[C:23]([OH:25])=[O:24])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67756817HCID 67756817, compound

Product 1

HCID 19004267HCID 19004267, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[[2-(2-naphthalenyloxy)ethyl]oxy]-alpha-oxobenzeneacetic acid sodium salt (3.0 g), dichloromethane (500 mL), and 1N hydrochloric acid (25 mL) was stirred for one hour until all solids dissolved. The layers were separated, the water layer was extracted 2×100 mL of dichloromethane and the organic layers were washed in turn with water. The combined organic layers were dried (Na2SO4), filtered and evaporated to give 2.8 g of crude product. Crystallization from dichloromethane-hexane provided 2.6 g of 4[[2- (2-naphthalenyloxy)ethyl]oxy]-alpha-oxobenzeneacetic acid, mp 170°-171° C.

Workup

  1. dissolutiondissolved
  2. customThe layers were separated
  3. extractionthe water layer was extracted 2×100 mL of dichloromethane
  4. washthe organic layers were washed in turn with water
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto give 2.8 g of crude product
  9. customCrystallization from dichloromethane-hexane

Sources & evidence

ORD record
ord-bebf8df2aab747569b893325e7af4e7d
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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