Butyl glycidyl ether → HCID 22141571, compound

HRID 1179101Notes

Reaction equation

HRID 1179101 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH:2]1[O:4][CH2:3]1.[SH-:10].[Na+].[NH4+].[Cl-]>C(O)(C)C.O>[S:10]([CH2:3][CH:2]([OH:4])[CH2:1][O:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH2:3][CH:2]([OH:4])[CH2:1][O:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

6

Conditions

Temperature
90 °C

Procedure

A solution of butyl glycidyl ether (2.91 g, 22.39 mmol) in isopropanol (5 mL) and H2O (1 mL) was added to sodium bisulfide (0.628 g, 11.20 mmol) under nitrogen in a 100 mL 3-neck round bottom flask equipped with a N2 inlet, a rubber septum, glass stopper and a magnetic stir bar. The mixture was heated at 90° C. and monitored for completion by gas chromatography/mass spectrometry for disappearance of starting materials and formation of the product. After 3 h, the reaction was judged to be complete. The mixture was cooled to ambient temperature and treated with saturated NH4Cl (5.0 mL) and extracted into ethyl acetate (50 mL). The solvent was dried (MgSO4), filtered, and evaporated in-vacuo to give the product, 1,1′-thiobis(3-butoxypropan-2-ol), which was identified by mass spectrometry as well as 1H and 13C NMR.

Workup

  1. customequipped with a N2 inlet
  2. temperatureThe mixture was cooled to ambient temperature
  3. extractionextracted into ethyl acetate (50 mL)
  4. dry with materialThe solvent was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in-vacuo

Sources & evidence

ORD record
ord-2edbd6c266bb44dbaf5fbf7f86c9a06c
Source dataset
uspto-grants-2007_10
Patent number
US07279447B2

Reaction notes

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