Formaldehyde → Formaldehyde

HRID 1659662Notes

Reaction equation

HRID 1659662 reaction equation
[CH2:1]=[O:2].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:10]1([OH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C([O-])(=O)C.[Zn+2].C([O-])(=O)C>[C:3]1([S:9][CH2:1][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[OH:16])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:1]=[O:2]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 996PhenolHCID 7969Thiophenol

Product 2

HCID 712FormaldehydeHCID 3813551HCID 3813551, compound

Reagents, catalysts & solvents 1

HCID 11192Zinc AcetateCatalyst

Procedure

4.5.10-3 mole of zinc acetate, in the form of an approximately 20% strength aqueous solution, 30 g of 96% pure paraformaldehyde ( 0.96 mole of CH2O) and 113.6 g of 97% pure thiophenol (1 mole) were added to 564 g (6 moles) of phenol at about 70° C. The mixture was then heated to the reflux temperature in the course of about 30 minutes and kept under these conditions for 7.5 hours (temperature of the mixture 154° to 132° C.). After this time, gas chromatography analysis gave a yield of 2-phenylthiomethylphenol of 81% of theory (relative to formaldehyde) and a ratio of 2- to 4-phenylthiomethylphenol of more than 99:1. The 2-phenylthiomethylphenol obtained on subsequent distillation at 140°-150° C./0.6-0.9 mm Hg was 98% pure.

Workup

  1. temperatureThe mixture was then heated to the reflux temperature in the course of about 30 minutes
  2. customtemperature of the mixture 154° to 132° C.

Sources & evidence

ORD record
ord-496705ac12da45dcb47df65a94738c51
Source dataset
uspto-grants-1981_12
Patent number
US04304940

Reaction notes

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