Hydrogen Peroxide → 3-Ethylbenzene-1,2-diol

HRID 218244Notes

Reaction equation

HRID 218244 reaction equation
[OH:1][C:2]1[C:9]([CH2:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1C=O.OO.C1CCCCC1.CC[O:22]C(C)=O>[OH-].[Na+].CCOC(C)=O>[OH:22][C:3]1[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10][CH3:11])[C:2]=1[OH:1]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 10125073HCID 10125073, compoundHCID 21867204Cyclohexane ethylacetate

Product 1

HCID 702783-Ethylbenzene-1,2-diol

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of crude 9 (ca. 80 mmol) in 2N NaOH (40 mL) cooled to 0-5° C., a solution of ca. 7% hydrogen peroxide (49 mL) was added dropwise over 30 min while maintaining the temperature at 20° C. The reaction was stirred for further 45 min then diluted with AcOEt (ca 250 mL), washed with HCl 2N (ca 50 mL). The aqueous layer was e-extracted with AcOEt and the combined organic extracts were washed with brine, and dried over sodium sulphate. The solvent was removed under reduced pressure to give a crude which was columned (cyclohexane:AcOEt 4:1) to give 6.4 g of 10 as a brown oil:

Workup

  1. washwashed with HCl 2N (ca 50 mL)
  2. washthe combined organic extracts were washed with brine
  3. dry with materialdried over sodium sulphate
  4. customThe solvent was removed under reduced pressure
  5. customto give a crude which

Sources & evidence

ORD record
ord-2e5b82af93e4435abf476e94d09ad76a
Source dataset
uspto-grants-2012_06
Patent number
US08198302B2

Reaction notes

Loading…