2-Mercaptoethanol → 2-Hydroxyethylthio-6-methyl-1,4-benzoquinone

HRID 344565

Reaction equation

HRID 344565 reaction equation
[CH3:1][C:2]1[C:3](=[O:9])[CH:4]=[CH:5][C:6](=[O:8])[CH:7]=1.[SH:10][CH2:11][CH2:12][OH:13]>C(O)C>[OH:13][CH2:12][CH2:11][S:10][C:4]1[C:3](=[O:9])[C:2]([CH3:1])=[CH:7][C:6](=[O:8])[CH:5]=1

Participants

4

Reactant 2

HCID 15672-MercaptoethanolHCID 11122Methyl-1,4-benzoquinone

Product 1

HCID 545702962-Hydroxyethylthio-6-methyl-1,4-benzoquinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl-p-benzoquinone 12.2 g, 0.1 mole) and 2-mercaptoethanol (3.9 g, 0.05 mole) are mixed in absolute ethanol (70 ml) under nitrogen and with stirring. The temperature rises to 50° C. The mixture is cooled in a bath of ice-water and left to stand, with stirring, for 2 hours at ambient temperature. The solution is concentrated under vacuum and the oil obtained is chromatographed on Silica 60 (eluent: dichloromethane). According to 1H and 13C NMR, a first fraction (3 g) is a 50/50 mixture of two products: 2-hydroxyethylthio-5-methyl-1,4-benzoquinone and 2-hydroxyethylthio-6-methyl-1,4-benzoquinone. A second fraction gives the expected product:

Workup

  1. customrises to 50° C
  2. waitleft
  3. stirringwith stirring, for 2 hours at ambient temperature
  4. concentrationThe solution is concentrated under vacuum
  5. customthe oil obtained
  6. customis chromatographed on Silica 60 (eluent: dichloromethane)
  7. additiona 50/50 mixture of two products

Sources & evidence

ORD record
ord-4daabdb621da4b75af8f4214a1b405c7
Source dataset
uspto-grants-1991_10
Patent number
US05053053

Linked notes

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