Benzoic Acid → Benzoyl chloride

HRID 1681578Notes

Reaction equation

HRID 1681578 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(NC2CCCCC2)CCCCC1.S(Cl)([Cl:25])=O>ClCCl>[C:1]([Cl:25])(=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 7582DicyclohexylamineHCID 24386Thionyl Chloride

Product 1

HCID 7412Benzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.80 g (9 mmoles) of 4-[3-(1-adamantyl)-4)-methoxybenzolythio]benzoic acid, 40 ml of dichloromethane, 1.8 ml (9 mmoles) of dicyclohexylamine are introduced into a round bottomed flask and are stirred for one hour. To the solution thus produced, are added 720 82 l (9.9 mmoles) of thionyl chloride and this is stirred at ambient temperature for two hours. This is then evaporated to dryness, taken up in 500 ml of ethyl ether, followed by filtering the dicyclohexylammonium chloride and then by evaporating the solvent. By this means are obtained 3.97 g (100% ) of crude 4-[3-(1-adamantyl)-4)-methoxybenzolythio]benzoic acid chloride which is used directly for the later synthesis.

Workup

  1. customTo the solution thus produced
  2. stirringthis is stirred at ambient temperature for two hours
  3. customThis is then evaporated to dryness
  4. filtrationby filtering the dicyclohexylammonium chloride
  5. customby evaporating the solvent

Sources & evidence

ORD record
ord-48e9520f5fce45099811a7e259c2d7f8
Source dataset
uspto-grants-1992_12
Patent number
US05173289

Reaction notes

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