Formaldehyde → HCID 86744917, compound

HRID 1086980Notes

Reaction equation

HRID 1086980 reaction equation
[CH:1]([C:5]1[CH:13]=[C:9]([C:10]([OH:12])=[O:11])[C:8]([OH:14])=[CH:7][CH:6]=1)([CH2:3][CH3:4])[CH3:2].[C:15]1([CH3:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH2:22]=[O:23].S(=O)(=O)(O)O>C(O)(=O)C>[CH:1]([C:5]1[CH:13]=[C:9]([C:10]([OH:12])=[O:11])[C:8]([OH:14])=[CH:7][CH:6]=1)([CH2:3][CH3:4])[CH3:2].[C:15]1([CH3:21])[C:16]([CH:22]=[O:23])=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 1140TolueneHCID 130269235-(Butan-2-yl)-2-hydroxybenzoic acid

Product 1

HCID 86744917HCID 86744917, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 19.4 parts of 5-sec-butylsalicylic acid, 18.4 parts of toluene, 3.8 parts of 87% paraformaldehyde and 30 parts of acetic acid was added 2.0 parts of 95% 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 5-sec-butylsalicylic acid-toluene-formaldehyde co-condensation product. 10 parts of the co-condensation product was added to 14 parts of aqueous 10% sodium hydroxide solution and dissolved at 80° C. The resulting solution was cooled to 40° C., and 2.4 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 dried to give 11.5 parts of zinc salt of 5-sec-butylsalicylic 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-1628748c93a248a8aa9894cd1dd313bf
Source dataset
uspto-grants-1991_07
Patent number
US05034370

Reaction notes

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