Benzaldehyde → Styrene Oxide

HRID 1290248Notes

Reaction equation

HRID 1290248 reaction equation
[SH3+].[CH:2](=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:10]1(C)C=CC=CC=1.C(O)CC.[OH-].[Na+]>>[O:9]1[CH2:10][CH:2]1[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 5

HCID 240BenzaldehydeHCID 10311-PropanolHCID 1140TolueneHCID 14798Sodium HydroxideHCID 3015009Sulfonium

Product 1

HCID 7276Styrene Oxide

Conditions

Temperature
50 °C

Procedure

To the sulphonium salt mixture was added benzaldehyde (13.52 g at 98%, 0.125 moles), toluene (92 g, 1 mole), and n-propanol (35.5 g, 0.59 moles) and the mixture stirred and heated to 50° C. Aqueous sodium hydroxide solution (32 g at 53%, 0.425 moles) was added and a temperature rise to 80° C. was observed (due to neutralisation of excess acid). The mixture was cooled to 70° C. and stirred at this temperature for 1 hour. The mixture was cooled, the organic layer separated, washed with water and dried over magnesium sulphate. Qualitative GC analysis showed 76% conversion to the title epoxide (by comparison with authentic sample).

Workup

  1. customto 80° C.
  2. temperatureThe mixture was cooled to 70° C.
  3. stirringstirred at this temperature for 1 hour
  4. temperatureThe mixture was cooled
  5. customthe organic layer separated
  6. washwashed with water
  7. dry with materialdried over magnesium sulphate

Sources & evidence

ORD record
ord-3ceb45a015d240ca837e527c58ae86fe
Source dataset
uspto-grants-1998_05
Patent number
US05750740

Reaction notes

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