Hydrochloric Acid → 5-Ethyl-2-(ethylsulfanyl)phenol

HRID 1154280Notes

Reaction equation

HRID 1154280 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)[CH3:2].[Al].[H][H].[CH2:13]([S:15]SCC)[CH3:14].Cl>>[CH2:13]([S:15][C:6]1[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][C:5]=1[OH:9])[CH3:14]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8077Diethyl disulfideHCID 121013-EthylphenolHCID 5359268AluminumHCID 178418361HCID 178418361, compound

Product 1

HCID 131993385-Ethyl-2-(ethylsulfanyl)phenol

Procedure

To freshly distilled 3-ethylphenol (100 grams, 0.82 moles), was added aluminum turnings (1.62 grams, 0.06 moles) and the mixture was heated at 175° to 195° C. until hydrogen evolution had ceased. Ethyldisulfide (63 grams, 0.515 moles) was then added in one portion at 150° C. This mixture was then heated at 175° to 180° C. for 18 hours and then for about 7 hours at 196° C. The resulting mixture was hydrolyzed with 3 N HCl, extracted with diethylether, washed with water and dried over magnesium sulfate. Distillation of the mixture followed by a redistillation through a packed column gave, after removal of by-products and starting materials, ⟦8.15⟧ 14.0 grams of 2-ethylthio-5-ethylphenol as verified by 1H and 13C NMR.

Workup

  1. temperatureThis mixture was then heated at 175° to 180° C. for 18 hours
  2. extractionextracted with diethylether
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. distillationDistillation of the mixture
  6. distillationfollowed by a redistillation through a packed column
  7. customgave
  8. customafter removal of by-products

Sources & evidence

ORD record
ord-ce606624cecd471f81ea8f81f73e57b5
Source dataset
uspto-grants-1984_12
Patent number
USRE031771

Reaction notes

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