Sodium Hydroxide → 2-(Oxiran-2-yl)-2,3-dihydro-1,4-benzodioxine

HRID 441426Notes

Reaction equation

HRID 441426 reaction equation
Br[CH2:2][C:3]([CH:5]1[O:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[O:7][CH2:6]1)=[O:4].[BH4-].[Na+].[OH-].[Na+]>CO>[O:10]1[C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[O:7][CH2:6][CH:5]1[CH:3]1[O:4][CH2:2]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 126085852-Bromo-1-(2,3-dihydro-1,4-benzodioxin-2-yl)ethan-1-one

Product 1

HCID 127367082-(Oxiran-2-yl)-2,3-dihydro-1,4-benzodioxine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The starting material is prepared as follows: To the solution of 42 g of 2-(2-bromoacetyl)-1,4-benzodioxan in 360 ml of methanol, 12 g of sodium borohydride are added while stirring and keeping the temperature below 10°. After 5 hours, the mixture is cooled to 0° and 13.2 g of sodium hydroxide in 150 ml of methanol are added and the mixture kept at -15° overnight. It is poured onto ice, extracted with diethyl ether, the extract washed with saturated aqueous sodium chloride, dried and evaporated, to yield the 1,4-benzodioxan-2-yl-ethyleneoxide.

Workup

  1. customThe starting material is prepared
  2. customthe temperature below 10°
  3. temperaturethe mixture is cooled to 0°
  4. waitthe mixture kept at -15° overnight
  5. additionIt is poured onto ice
  6. extractionextracted with diethyl ether
  7. washthe extract washed with saturated aqueous sodium chloride
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-d8c4e080ff8a4bcd83a9d4c62ed02632
Source dataset
uspto-grants-1977_08
Patent number
US04039676

Reaction notes

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