p-Toluenesulfonic acid → HCID 86744918, compound

HRID 1086981Notes

Reaction equation

HRID 1086981 reaction equation
[CH2:1]([C:10]1[CH:18]=[C:14]([C:15]([OH:17])=[O:16])[C:13]([OH:19])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[C:20]1([CH3:27])[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=1.[CH2:28]1OCOC[O:29]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(=O)C>[CH2:1]([C:10]1[CH:18]=[C:14]([C:15]([OH:17])=[O:16])[C:13]([OH:19])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[C:20]1([CH3:27])[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[C:21]=1[CH:28]=[O:29]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 7929M-XyleneHCID 80811,3,5-TrioxaneHCID 15745145HCID 15745145, compound

Product 1

HCID 86744918HCID 86744918, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 26.4 parts of 5-nonylsalicylic acid, 5.9 parts of m-xylene, 3.4 parts of sym-trioxane and 15 parts of acetic acid was added 4.0 parts of p-toluenesulfonic acid (catalyst). After being heated under reflux for 5 hours, the reaction mixture was washed with water, and unreacted m-xylene and water were removed by vacuum distillation to give 38 parts of 5-nonylsalicylic acid-m-xylene-formaldehyde co-condensation product. To 10 parts of the co-condensation product was added gradually a mixture of 0.9 parts of zinc oxide and 0.5 parts of ammonium hydrogencarbonate at a temperature of 150° C. After the completion of the addition, the reaction was allowed to proceed for an additional hour at 150° C. to give 10.8 parts of zinc salt of 5-nonylsalicylic acid-m-xylene-formaldehyde co-condensation product.

Workup

  1. temperatureAfter being heated
  2. temperatureunder reflux for 5 hours
  3. washthe reaction mixture was washed with water, and unreacted m-xylene and water
  4. customwere removed by vacuum distillation

Sources & evidence

ORD record
ord-0c04f199f54741e59064aaf1f62ae2e6
Source dataset
uspto-grants-1991_07
Patent number
US05034370

Reaction notes

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