Phenol → 2-(Ethylthio)phenol

HRID 745695Notes

Reaction equation

HRID 745695 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]([S:10]SCC)[CH3:9].C(S)C>C(O)CC.CCCO.CCCO.CCCO.CCCO.[Zr].[Zr]>[CH2:8]([S:10][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[OH:7])[CH3:9]

Participants

7

Reactant 3

HCID 996Phenol2×HCID 6343EthanethiolHCID 8077Diethyl disulfide

Product 1

HCID 1224072-(Ethylthio)phenolYield 41.2%

Reagents, catalysts & solvents 3

HCID 23995ZirconiumCatalystHCID 3539967Zirconium n-propoxideCatalystHCID 10311-PropanolSolvent2×

Conditions

Temperature
200 °C

Procedure

To phenol (35.3 g, 0.37 moles) was added 10.6 g of zirconium n-propoxide in n-propanol consisting of 21.6% zirconium (0.025 mole) and 10.8% free n-propanol. The mixture was distilled at atmospheric pressure removing n-propanol. Ethyl disulfide (30.6 g, 0.25 moles) was added, and the mixture was heated under nitrogen while ethyl mercaptan was removed continuously by distillation. Heating was continued for a total of 6.5 hours during which temperature slowly increased to 200° C. Distillation of the mixture at 0.5 mm mercury to a maximum head temperature of 84° C. yielded 31.7 g of distillate. GC analysis indicated the distillate contained 12.4 g of phenol (35% recovered) and 15.9 g of ortho-(ethylthio)phenol (41% yield).

Workup

  1. distillationThe mixture was distilled at atmospheric pressure
  2. customremoving n-propanol
  3. customwas removed continuously by distillation
  4. temperatureHeating
  5. customwas continued for a total of 6.5 hours during which temperature
  6. distillationDistillation of the mixture at 0.5 mm mercury to a maximum head temperature of 84° C.
  7. customyielded 31.7 g of distillate

Sources & evidence

ORD record
ord-d357c6a9d9b74e699f7a3c75a3f7694f
Source dataset
uspto-grants-1986_07
Patent number
US04599451

Reaction notes

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