Sodium Hydroxide → 2,2-diethoxy-ethanethiol

HRID 1700166Notes

Reaction equation

HRID 1700166 reaction equation
C1(C([S:9][CH2:10][CH:11]([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])=O)C=CC=CC=1.[OH-].[Na+]>C1COCC1.O>[SH:9][CH2:10][CH:11]([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11536175HCID 11536175, compound

Product 1

HCID 109426222,2-diethoxy-ethanethiol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

The preceding thiobenzoyl derivative (V) (17.2 g) was dissolved in 100 ml THF followed by the addition of 6 g NaOH in 20 ml H2O. The mixture was refluxed under N2 for 15 h, then cooled and diluted with water (200 ml) and the product extracted with ether (3×200 ml). The extract was dried, the solvent removed in vacuo and the residue distilled in vacuo to yield 7.1 g of pure (VI), b.p. 60-62°/18 mm. It was characterized by 1H NMR δ(ppm in CDCl3):

Workup

  1. temperatureThe mixture was refluxed under N2 for 15 h
  2. temperaturecooled
  3. extractionthe product extracted with ether (3×200 ml)
  4. customThe extract was dried
  5. customthe solvent removed in vacuo
  6. distillationthe residue distilled in vacuo

Sources & evidence

ORD record
ord-e622936fce6e4257b3e5625976ffcab1
Source dataset
uspto-grants-2002_02
Patent number
US06350753B1

Reaction notes

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