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

HRID 1283402Notes

Reaction equation

HRID 1283402 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.[Na+].[Cl-:21].[Na+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].[OH-].[Na+]>Cl.O>[Cl:21][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 656671Sodium PyrosulfiteHCID 20352627HCID 20352627, compoundHCID 23668193Sodium Nitrite

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 nitrite (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 hyroxide (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-6321e7c518b0429b885f1bd8438bf154
Source dataset
uspto-grants-1976_08
Patent number
US03975388

Reaction notes

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