4-Hydroxybenzoic Acid → 4-hydroxybenzoyl Chloride

HRID 236555Notes

Reaction equation

HRID 236555 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][CH:3]=1.S(Cl)([Cl:13])=O>CN(C)C=O>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:13])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1354-Hydroxybenzoic AcidHCID 24386Thionyl Chloride

Product 1

HCID 110519074-hydroxybenzoyl Chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Hydroxybenzoic acid (11.04 g.) was heated under reflux with thionyl chloride (80 ml.) containing dimethylformamide (0.1 ml.) for 2 hours. The solution obtained was evaporated. The residue was dissolved in toluene and the subsequent solution was evaporated. The residue obtained (which contained 4-hydroxybenzoyl chloride) was dissolved in methylene chloride (80 ml.). The solution obtained was treated dropwise with 1,2,3,6-tetrahydropyridine to pH7 with stirring and ice-cooling. The mixture was further stirred at 25° C. after the addition was complete for 2 hours and then evaporated. The residue was stirred with water and the solid was collected by filtration and then washed with water and acetone. After recrystallisation from a mixture of ethanol and ethyl acetate, there was obtained 1-(4-hydroxybenzoyl)-1,2,3,6-tetrahydropyridine (11.3 g.), m.p. 202°-206° C.

Workup

  1. customThe solution obtained
  2. customwas evaporated
  3. dissolutionThe residue was dissolved in toluene
  4. customthe subsequent solution was evaporated

Sources & evidence

ORD record
ord-7c02c94a189a441aaba74c546d49bfa5
Source dataset
uspto-grants-1987_02
Patent number
US04645771

Reaction notes

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