Sulfuric Acid → 1-Phenyl-1,2-ethanediol

HRID 347616

Reaction equation

HRID 347616 reaction equation
[OH:1]S(O)(=O)=O.[CH2:6]1[O:14][CH:7]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C>[C:8]1([CH:7]([OH:1])[CH2:6][OH:14])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 7276Styrene Oxide

Product 1

HCID 71491-Phenyl-1,2-ethanediolYield 91%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 3283Diethyl EtherSolvent

Procedure

A 2 l stirrer fitted with reflux condenser, thermometer and dropping funnel was charged with 600 g of 0.1% strength H2SO4 and 2 g of tetrabutylammonium hydrogensulfate, and then, at 20° C. to 25° C., 200 g (1.67 mol) of styrene oxide (2) were added over the course of 1 h. When the dropwise addition was complete, the mixture was then stirred for 2 h and then worked up. 200 ml of diethyl ether were added to the reaction mixture, and the organic phase was washed until neutral with sodium carbonate solution and water, and dried over Na2SO4, and the solvent was distilled off under reduced pressure, leaving 223 g of crude product (91% pure according to GC).

Workup

  1. customA 2 l stirrer fitted
  2. temperaturewith reflux condenser
  3. additionWhen the dropwise addition
  4. washthe organic phase was washed until neutral with sodium carbonate solution and water
  5. dry with materialdried over Na2SO4
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1707c85e4342412397a83f9aa5f4967d
Source dataset
uspto-grants-2007_02
Patent number
US07176176B2

Linked notes

Loading…