1-Bromo-2-(methylsulfanyl)ethane → HCID 13386372, compound

HRID 637539Notes

Reaction equation

HRID 637539 reaction equation
[CH2:1]([O:3][CH:4]([CH2:14][O:15][CH2:16][CH3:17])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].[CH3:18][S:19][CH2:20][CH2:21]Br>[OH-].[K+].C(O)C>[CH3:18][S:19][CH2:20][CH2:21][O:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][CH:4]([O:3][CH2:1][CH3:2])[CH2:14][O:15][CH2:16][CH3:17])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 5543651-Bromo-2-(methylsulfanyl)ethaneHCID 202570834-(2,3-Diethoxypropoxy)phenol

Product 1

HCID 13386372HCID 13386372, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

A 2.40 g quantity of 4-(2,3-diethoxypropoxy)phenol was dissolved in 0.56 g of potassium hydroxide and 10 ml of 90% ethanol. To the solution was added 1.55 g of 2-methylmercaptoethyl bromide. The mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated and the residue was extracted with chloroform. The chloroform layer was washed with water, dewatered with Glauber's salt and concentrated. The residue was distilled at reduced pressure, giving 2.95 g of 2-{4-(2,3-diethoxypropoxy)phenoxy}ethyl methyl sulfide in 93.9% yield, b.p. 176° to 177° C./l to 2 mmHg.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionthe residue was extracted with chloroform
  3. washThe chloroform layer was washed with water
  4. concentrationconcentrated
  5. distillationThe residue was distilled at reduced pressure

Sources & evidence

ORD record
ord-8f897feda5844471a015f17f86a7ab5b
Source dataset
uspto-grants-1985_12
Patent number
US04556737

Reaction notes

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