Water → 2-[(2-Hydroxyethyl)thio]ethyl benzoate

HRID 1926078Notes

Reaction equation

HRID 1926078 reaction equation
[SH:1][CH2:2][CH2:3][OH:4].[C:5]([O:13][CH2:14][CH2:15]I)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(C(C)C)C(C)C)C.O>CN(C)C=O>[C:5]([O:13][CH2:14][CH2:15][S:1][CH2:2][CH2:3][OH:4])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 15672-MercaptoethanolHCID 81531DiisopropylethylamineHCID 125101182-Iodoethyl Benzoate

Product 1

HCID 544395062-[(2-Hydroxyethyl)thio]ethyl benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-mercaptoethanol (1.52 mL), 2-iodoethyl benzoate (6.00 g) and ethyldiisopropylamine (4.53 mL) in N,N-dimethylformamide (60 mL) was stirred at 40° C. for 3 days. Water was added to the reaction system and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (eluent, hexane:ethyl acetate=4:1→3:7) to give the title compound (3.77 g) as an orange oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified by silica gel column chromatography (eluent, hexane:ethyl acetate=4:1→3:7)

Sources & evidence

ORD record
ord-f7d4e0c90c66485092bc62cf7a41a35e
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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