Sodium Chloride → Benzenebutanoic acid, 3-chloro-4-methoxy-gamma-oxo-

HRID 372002Notes

Reaction equation

HRID 372002 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:5]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[O:6].[N+]([O-])([O-])=O.[Na+].[Cl-:22].[Na+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].[OH-].[Na+]>Cl.O>[Cl:22][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:5]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[O:6]

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 24268Sodium NitrateHCID 656671Sodium PyrosulfiteHCID 20352627HCID 20352627, compound

Product 1

HCID 10060312Benzenebutanoic acid, 3-chloro-4-methoxy-gamma-oxo-

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Procedure

A solution of 3-(3-amino-4-methoxybenzoyl) propionic acid (5 g.) in concentrated hydrochloric acid (25 ml.) was diazotised at 0° C by the addition of a solution of sodium nitrate (1.54 g.) in water (5 ml.). This diazo solution was added with stirring to a solution containing hydrated copper sulphate (6.3 g.) and sodium chloride (5.4 g.) in water (20 ml.) to which had been added a solution containing sodium metabisulphite (1.4 g.) and sodium hydroxide (0.9 g.) in water (10 ml.). The mixture was then heated on the steam bath for 30 minutes when a solid separated. The mixture was cooled, the solid collected and washed with cold water. It was crystallised from methanol to yield the product (4.2 g.), m.p. 187°-189° C.

Workup

  1. additionhad been added a solution
  2. temperatureThe mixture was then heated on the steam bath for 30 minutes when a solid
  3. customseparated
  4. temperatureThe mixture was cooled
  5. customthe solid collected
  6. washwashed with cold water
  7. customIt was crystallised from methanol
  8. customto yield the product (4.2 g.), m.p. 187°-189° C.

Sources & evidence

ORD record
ord-1ca3827a9bcf49feb59589f166183775
Source dataset
uspto-grants-1978_05
Patent number
US04088762

Reaction notes

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