Salicylic Acid → HCID 86744923, compound

HRID 1086986Notes

Reaction equation

HRID 1086986 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[C:11]1([CH3:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:18]=[O:19].S(=O)(=O)(O)O>C(O)(=O)C>[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[C:11]1([CH3:17])[C:12]([CH:18]=[O:19])=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 338Salicylic AcidHCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 1140Toluene

Product 1

HCID 86744923HCID 86744923, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 13.8 parts of salicylic acid, 18.4 parts of toluene, 6.9 parts of 87% paraformaldehyde and 30 parts of acetic acid was added 1.0 part of sulfuric acid (catalyst). After being heated under reflux for 4 hours, the reaction mixture was washed with water, and unreacted toluene and water were removed by vacuum distillation to give 31 parts of salicylic acid-toluene-formaldehyde co-condensation product. 10 parts of the co-condensation product was added to 41 parts of aqueous 10% sodium hydroxide solution and dissolved at 80° C. The resulting solution was cooled to 40° C., and 7.0 parts of zinc chloride was added thereto. After the reaction had been allowed to proceed at 40° C. for 1 hour, precipitates formed were collected by filtration, washed with water and then dried to give 12 parts of zinc salt of salicylic acid-toluene-formaldehyde co-condensation product.

Workup

  1. temperatureAfter being heated
  2. temperatureunder reflux for 4 hours
  3. washthe reaction mixture was washed with water, and unreacted toluene and water
  4. customwere removed by vacuum distillation

Sources & evidence

ORD record
ord-d89bba424e9e41b1b0129bac4932c50c
Source dataset
uspto-grants-1991_07
Patent number
US05034370

Reaction notes

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