3-Chlorobenzoic Acid → HCID 178520910, compound

HRID 259290Notes

Reaction equation

HRID 259290 reaction equation
[CH:1]1([S:7][CH2:8][CH2:9][C:10]([C-:12]2[CH:16]=[CH:15][CH:14]=[CH:13]2)=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH-:17]1[CH:21]=[CH:20][CH:19]=[CH:18]1.[Fe+2:22].ClC1C=C(C=CC=1)C(O)=[O:28]>C(Cl)(Cl)Cl>[CH:1]1([S:7]([CH2:8][CH2:9][C:10]([C-:12]2[CH:13]=[CH:14][CH:15]=[CH:16]2)=[O:11])=[O:28])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1.[CH-:17]1[CH:21]=[CH:20][CH:19]=[CH:18]1.[Fe+2:22]

Participants

4

Reactant 2

HCID 4473-Chlorobenzoic AcidHCID 178520905HCID 178520905, compound

Product 1

HCID 178520910HCID 178520910, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-(Cyclohexylthio)propionylferrocene (1.3g, 0.00366M) was dissolved in chloroform (30 ml) and the solution was cooled in ice/water. m-Chlorobenzoic acid (0.63g, 0.00366M) was then added slowly with stirring. Following the addition, stirring was continued at room temperature for 3 hours, and the resulting solution was washed with dilute sodium bicarbonate solution and water, before being dried over anhydrous sodium sulphate. Removal of the solvent on a rotary evaporator yielded a red oil which subsequently crystallised as orange needles of the title compound (1.15g) mp = 90°-1°.

Workup

  1. additionthe addition
  2. stirringstirring
  3. washthe resulting solution was washed with dilute sodium bicarbonate solution and water
  4. dry with materialbefore being dried over anhydrous sodium sulphate
  5. customRemoval of the solvent
  6. customon a rotary evaporator
  7. customyielded a red oil which
  8. customsubsequently crystallised as orange needles of the title compound (1.15g) mp = 90°-1°

Sources & evidence

ORD record
ord-ad57436668e540598077921be96f0cd3
Source dataset
uspto-grants-1977_07
Patent number
US04036983

Reaction notes

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