Hydrochloric Acid → 2-(2-Chlorobenzoyl)benzoic acid

HRID 328685Notes

Reaction equation

HRID 328685 reaction equation
S(=O)(=O)(O)O.N([O-])=O.[Na+].N[C:11]1[CH:27]=[CH:26][CH:25]=[CH:24][C:12]=1[C:13]([C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=[O:18])=[O:14].[Cl-:28].[Na+].Cl>O>[Cl:28][C:11]1[CH:27]=[CH:26][CH:25]=[CH:24][C:12]=1[C:13]([C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=[O:18])=[O:14]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 708472-(2-Aminobenzoyl)benzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 150757962-(2-Chlorobenzoyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 250 ml. of concentrated sulfuric acid was added, with stirring and slight cooling, 37.5 g. (0.545 mole) of sodium nitrite. To this was added 120.5 g. (0.50 mole) of 2-(2-aminobenzoyl)benzoic acid at such a rate that the temperature of the reaction mixture remained between 30°-40°. After the addition was complete the reaction mixture was stirred for one hour and then poured into one liter of ice and water and filtered. The filtrate was added rapidly to a stirred solution of 55 g. (0.555 mole) of cuprous chloride, 150 g. of sodium chloride, 250 ml. of concentrated hydrochloric acid and 300 ml. of water. The precipitated gum was extracted with chloroform and the extracts were washed twice with water, dried over anhydrous sodium sulfate and evaporated under vacuo to leave a red oil which crystallized upon scratching. Recrystallization from 200 ml. of ethyl acetate gave 2-(2-chlorobenzoyl)benzoic acid as a pink solid. A sample recrystallized three times from ethyl acetate gave colorless prisms, double m.p. 112°-116° and 124°-126°.

Workup

  1. additionTo this was added 120.5 g
  2. customremained between 30°-40°
  3. additionAfter the addition
  4. stirringwas stirred for one hour
  5. filtrationfiltered
  6. additionThe filtrate was added rapidly to a stirred solution of 55 g
  7. extractionThe precipitated gum was extracted with chloroform
  8. washthe extracts were washed twice with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. customevaporated under vacuo
  11. customto leave a red oil which
  12. customcrystallized
  13. customRecrystallization from 200 ml

Sources & evidence

ORD record
ord-4dc23ad433ae4bf9a6d9d3b6a385a2c3
Source dataset
uspto-grants-1977_04
Patent number
US04018765

Reaction notes

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