Formaldehyde → Formaldehyde

HRID 2198591

Reaction equation

HRID 2198591 reaction equation
[C:1]1([OH:7])C=CC=CC=1.[CH2:8]=[O:9].C(S)C.C(SC[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23])C>C([O-])(=O)C.[Zn+2].C([O-])(=O)C>[CH2:1]=[O:7].[OH:9][CH2:8][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 996PhenolHCID 6343EthanethiolHCID 5221672-[(Ethylsulfanyl)methyl]phenol

Product 2

HCID 712FormaldehydeHCID 5146Salicyl Alcohol

Reagents, catalysts & solvents 1

HCID 11192Zinc AcetateCatalyst

Procedure

A mixture of 450 g of phenol, 0.8 g of zinc acetate and 24 g of paraformaldehyde was warmed for 6 hours to 70° C. in a flask equipped with a stirrer and a reflux condenser. 49.6 g of ethylmercaptan were then added to the reaction mixture and the reaction temperature in the flask was raised progressively so that there was always a slight reflux. After about 12 hours, when a final temperature of 120° C. had been reached, the reaction was stopped by cooling and the reaction mixture was worked up by distillation. The phenol could be re-used in a subsequent reaction. The yield of isolated 2-ethylthiomethyl-phenol was 70% of theory, relative to paraformaldehyde, and about 95%, relative to the 2-hydroxymethyl-phenol formed as an intermediate.

Workup

  1. temperaturewas warmed for 6 hours to 70° C. in a flask
  2. customequipped with a stirrer and a reflux condenser
  3. temperaturethe reaction temperature in the flask was raised progressively so that there
  4. customtemperature of 120° C.
  5. temperatureby cooling
  6. distillationthe reaction mixture was worked up by distillation
  7. customThe phenol could be re-used in a subsequent reaction

Sources & evidence

ORD record
ord-ed670bfdc70b4db5afbdebd52c65f805
Source dataset
uspto-grants-1982_11
Patent number
US04358616

Linked notes

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