2-Mercaptoethanol → HCID 14551708, compound

HRID 620806Notes

Reaction equation

HRID 620806 reaction equation
[Cl:1][CH2:2][CH:3](Cl)[CH2:4][C:5](=[O:9])[CH2:6][CH2:7][CH3:8].[SH:11][CH2:12][CH2:13]O.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:6]([C:5]1[O:9][CH2:13][CH2:12][S:11][C:4]=1[CH2:3][CH2:2][Cl:1])[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 8471TriethylamineHCID 12287644HCID 12287644, compound

Product 1

HCID 14551708HCID 14551708, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 0.056 mole (10 g.) of 1,2-dichloro-4-heptanone and 0.06 mole (5 g.) 2-mercaptoethanol was stirred in 200 ml toluene; 0.06 mole (6 g.) triethylamine was added dropwise. The mixture was stirred at room temperature overnight, then washed with dilute hydrochloric acid and refluxed with 0.5 mole PTS, using a Dean-Stark trap to remove water for 7 hours. The PTSA solution was washed with 5% sodium bicarbonate, dried, filtered and the solvent was removed. The product was distilled; bp 80°-85°/0.05 mm. Yield 23%.

Workup

  1. washwashed with dilute hydrochloric acid
  2. temperaturerefluxed with 0.5 mole PTS
  3. customto remove water for 7 hours
  4. washThe PTSA solution was washed with 5% sodium bicarbonate
  5. customdried
  6. filtrationfiltered
  7. customthe solvent was removed
  8. distillationThe product was distilled

Sources & evidence

ORD record
ord-537ac1a6693c4a29bdc53444272fb41a
Source dataset
uspto-grants-1989_04
Patent number
US04822813

Reaction notes

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