Hydrochloric Acid → HCID 25766436, compound

HRID 582222Notes

Reaction equation

HRID 582222 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O:19]CC)=[O:18])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl>CO.O1CCOCC1.[OH-].[Na+]>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=[O:18])=[CH:12][CH:11]=2)=[CH:22][CH:23]=1)([O-:3])=[O:2]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 54127229HCID 54127229, compound

Product 1

HCID 25766436HCID 25766436, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

After 3.15 g (10.0 mmol) of ethyl 4-(4-nitrobenzyloxy)phenylacetate were dissolved in a mixed solvent of 50 ml of methanol and 50 ml of 1,4-dioxane, 70 ml of a 1 N aqueous solution of sodium hydroxide were added, and the resultant mixture was stirred at room temperature for 2 hours. After completion of the reaction, the reaction mixture was acidified with diluted hydrochloric acid and extracted with chloroform. The resultant extract was then dried over anhydrous sodium sulfate. After distilling off chloroform under reduced pressure, deposited crystals were ground with ether, thereby obtaining 2.64 g (yield: 92.0%) of the intended compound as crystals.

Workup

  1. additionwere added
  2. customAfter completion of the reaction
  3. extractionextracted with chloroform
  4. extractionThe resultant extract
  5. dry with materialwas then dried over anhydrous sodium sulfate
  6. distillationAfter distilling off chloroform under reduced pressure

Sources & evidence

ORD record
ord-f069085e2729440181f41736841adb5a
Source dataset
uspto-grants-1999_07
Patent number
US05922767

Reaction notes

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