2-(Methylsulfanyl)acetyl chloride → 2-{4-(2,3-Dihydroxypropoxy)phenoxy}ethyl methyl sulfide

HRID 637538Notes

Reaction equation

HRID 637538 reaction equation
[OH:1][CH:2]([CH2:12][OH:13])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[CH3:14][S:15][CH2:16][C:17](Cl)=O>[OH-].[Na+].CO>[CH3:14][S:15][CH2:16][CH2:17][O:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH:2]([OH:1])[CH2:12][OH:13])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 111262562-(Methylsulfanyl)acetyl chlorideHCID 129410344-(2,3-Dihydroxypropoxy)phenol

Product 1

HCID 133863712-{4-(2,3-Dihydroxypropoxy)phenoxy}ethyl methyl sulfideYield 87.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A 1.84 g quantity of 4-(2,3-dihydroxypropoxy)phenol was dissolved in 0.40 g of sodium hydroxide and 10 ml of 90% methanol. To the solution was added 1.11 g of 2-methylmercaptoacetyl chloride, and the mixture was refluxed for 6 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 recrystallized from benzene-petroleum ether, giving 2.25 g of 2-{4-(2,3-dihydroxypropoxy)phenoxy}ethyl methyl sulfide in 87.2% yield, M.P. 59° to 61° C.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. concentrationThe reaction mixture was concentrated
  3. extractionthe residue was extracted with chloroform
  4. washThe chloroform layer was washed with water
  5. concentrationconcentrated
  6. customThe residue was recrystallized from benzene-petroleum ether

Sources & evidence

ORD record
ord-e21cb30aa3cf44298855365942312f14
Source dataset
uspto-grants-1985_12
Patent number
US04556737

Reaction notes

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