2-Chloroethanol → HCID 2192654, compound

HRID 742526Notes

Reaction equation

HRID 742526 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([SH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+].O.Cl[CH2:19][CH2:20][OH:21].[CH2:22]([OH:24])[CH3:23]>>[OH:21][CH2:20][CH2:19][S:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14][CH2:23][CH2:22][OH:24])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 342-ChloroethanolHCID 702Ethanol2×HCID 962WaterHCID 14798Sodium HydroxideHCID 813994,4'-Thiobiphenyl

Product 1

HCID 2192654HCID 2192654, compound

Procedure

A mixture of 4,4'-dimercaptobiphenyl (41.7 grams, 0.19 mole), 50% NaOH [31.2 grams (15.6 grams, 0.39 mole NaOH)], water (100 mL) and 2 β ethanol (60 mL) was heated under nitrogen under stirring while 2-chloroethanol (31.5 grams, 0.39 mole) was added dropwise at reflux. When addition was completed, additional 2 β ethanol (60 mL) was added to facilitate stirring. After being heated an additional 2.0 hours at reflux, the reaction mixture was allowed to cool and the product was collected by vacuum filtration, washed with water and dried in air.

Workup

  1. temperaturewas heated under nitrogen
  2. additionwas added dropwise
  3. temperatureat reflux
  4. additionWhen addition
  5. temperatureAfter being heated an additional 2.0 hours
  6. temperatureat reflux
  7. temperatureto cool
  8. filtrationthe product was collected by vacuum filtration
  9. washwashed with water
  10. customdried in air

Sources & evidence

ORD record
ord-5f1f2dec0efd4cd886c19d8a460f7d88
Source dataset
uspto-grants-1996_09
Patent number
US05554720

Reaction notes

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