Sodium Hydroxide → HCID 19004457, compound

HRID 2225628Notes

Reaction equation

HRID 2225628 reaction equation
C[O:2][C:3](=[O:20])[C:4](=[O:19])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=1.[OH-].[Na+]>CO>[C:13]1([CH2:12][O:11][C:8]2[CH:9]=[CH:10][C:5]([C:4](=[O:19])[C:3]([OH:20])=[O:2])=[CH:6][CH:7]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 24974156HCID 24974156, compound

Product 1

HCID 19004457HCID 19004457, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 4-[(phenylmethyl)oxy]-alpha-oxobenzeneacetic acid methyl ester (0.53 g) in methanol (5 mL) and 0. SN sodium hydroxide (8 mL) were heated on the steam bath for 0.5 hours while methanol was distilled out. The resulting mixture containing solid sodium salt was cooled, concentrated to remove the organic solvents, acidified with 1N hydrochloric acid (4 mL), and extracted with diethyl ether (3×25 mL). The organic layers were washed in turn with water (2×10 mL) and the combined organic layers were dried (Na2SO4), filtered, and evaporated to give 0.5 g of crude product. Crystallization from benzene-hexane provided 0.45 g of 4-[(phenylmethyl)oxy]-alpha-oxobenzeneacetic acid, mp 97°-98° C.

Workup

  1. distillationwas distilled out
  2. additionThe resulting mixture containing solid sodium salt
  3. temperaturewas cooled
  4. concentrationconcentrated
  5. customto remove the organic solvents
  6. extractionextracted with diethyl ether (3×25 mL)
  7. washThe organic layers were washed in turn with water (2×10 mL)
  8. dry with materialthe combined organic layers were dried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated
  11. customto give 0.5 g of crude product
  12. customCrystallization from benzene-hexane

Sources & evidence

ORD record
ord-7903304aced64c938f18a74b5bf9ad21
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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