Hydrochloric Acid → 4-(3-Formyl-4-nitro-phenoxy)-butyric acid

HRID 2308691Notes

Reaction equation

HRID 2308691 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([O:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10])=[O:2].[OH-].[Na+].Cl.CCOCC>C(O)C>[CH:1]([C:3]1[CH:4]=[C:5]([O:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 10588876Ethyl 4-((3-formyl-4-nitrophenyl)oxy)butyrate

Product 1

HCID 27592274-(3-Formyl-4-nitro-phenoxy)-butyric acidYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-(3-formyl-4-nitrophenyl)oxybutyrate (65 g) in ethanol (400 ml) was added 3N NaOH (100 ml) in small portions. After 30 minutes at room temperature the reaction mixture was acidified with concentrated HCl and the ethanol evaporated. The aqueous residue was extracted with ethyl acetate (4×200 ml). The combined organic layers were washed with brine (2×200 ml), dried over Na2SO4, filtered and evaporated to give a light yellow solid. Trituration with ether afforded 4-(3-formyl-4-nitrophenyl)oxybutyric acid (55 g), m.p. 109°-110° C.

Workup

  1. customthe ethanol evaporated
  2. extractionThe aqueous residue was extracted with ethyl acetate (4×200 ml)
  3. washThe combined organic layers were washed with brine (2×200 ml)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a light yellow solid

Sources & evidence

ORD record
ord-c83063acda71429b89ac7447d27952e0
Source dataset
uspto-grants-1987_09
Patent number
US04690925

Reaction notes

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