2-Chloroethanol → 2-((2-Phenylethyl)thio)ethanol

HRID 2108132Notes

Reaction equation

HRID 2108132 reaction equation
[CH2:1]([SH:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[K+].Cl[CH2:13][CH2:14][OH:15].Cl>CO>[C:3]1([CH2:2][CH2:1][S:9][CH2:13][CH2:14][OH:15])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 781262-Phenylethanethiol

Product 1

HCID 196052-((2-Phenylethyl)thio)ethanolYield 68.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Phenethylmercaptan (2.0 g) and potassium hydroxide (0.81 g) in methanol (15 ml) were stirred together under nitrogen for 15 min. 2-Chloroethanol (2.33 g) was added and the solution stirred under nitrogen for 6 h. 2N hydrochloric acid was added to acidify the mixture to pH5, and the methanol evaporated in vacuo. The residue was partitioned between water (100 ml) and diethyl ether (100 ml) and separated. The aqueous phase was re-extracted with diethyl ether (100 ml) and the combined ethereal layers dried and evaporated in vacuo to give an oil. Purification by FCC eluting with System F (3:1) gave the title compound (1.80 g) as a colourless oil. T.l.c. (diethyl ether) Rf 0.70

Workup

  1. customthe methanol evaporated in vacuo
  2. customThe residue was partitioned between water (100 ml) and diethyl ether (100 ml)
  3. customseparated
  4. extractionThe aqueous phase was re-extracted with diethyl ether (100 ml)
  5. customthe combined ethereal layers dried
  6. customevaporated in vacuo
  7. customto give an oil
  8. customPurification by FCC
  9. washeluting with System F (3:1)

Sources & evidence

ORD record
ord-9a4b079a89b64cab805095bc3591b11b
Source dataset
uspto-grants-1990_06
Patent number
US04937268

Reaction notes

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