Sodium Hydroxide → HCID 16781333, compound

HRID 456588

Reaction equation

HRID 456588 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1C=O.[CH3:13][O:14]S([O-])(=O)=O.[CH3:19][S+](C)C.[OH-].[Na+]>ClCCl>[O:14]1[CH2:13][CH:19]1[C:8]1[CH:9]=[CH:10][C:5]2[O:4][CH2:3][CH2:2][O:1][C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 1917252-Formyl-1,4-benzodioxaneHCID 2760871Trimethylsulfonium methyl sulfate

Product 1

HCID 16781333HCID 16781333, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1,4-benzodioxanecarboxaldehyde [RN 29668-44-8](1.5 g, 9.14 mmol), trimethylsulfonium methyl sulfate (2.24 g, 11.9 mmol), dichloromethane (35 ml) and 50% aqueous sodium hydroxide (5 ml) were vigorously stirred for 70 hours. The mixture was partitioned between water and diethyl ether and the layers separated. The aqueous phase was extracted with diethyl ether. The combined organic phases were washed with water, brine, then dried over magnesium sulfate and evaporated to give crude 6-oxiranyl-2,3-dihydro-benzo[1,4]dioxine (1.64 g, 100%).

Workup

  1. customThe mixture was partitioned between water and diethyl ether
  2. customthe layers separated
  3. extractionThe aqueous phase was extracted with diethyl ether
  4. washThe combined organic phases were washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-6c474692bdbe4f82b3b6d1648d1a2bc8
Source dataset
uspto-grants-2007_03
Patent number
US07186730B2

Linked notes

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