Dichloromethane → HCID 19900861, compound

HRID 1639281Notes

Reaction equation

HRID 1639281 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[O:5][CH:6]=[CH:7][CH:8]=1.[C:9](=[O:12])([O-:11])[O-].[Na+].[Na+].[CH2:15](Cl)Cl.BrBr>CO>[CH3:1][O:2][CH2:3][C:4]1([O:5][CH3:6])[CH:8]=[CH:7][CH:9]([O:12][CH3:15])[O:11]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 24408Bromine2×HCID 61661Furan, 2-(methoxymethyl)-

Product 1

HCID 19900861HCID 19900861, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2-Methoxymethyl furan (120.4 g, 1.07 moles), anhydrous methanol (250 ml, 6.18 moles), anhydrous sodium carbonate (190 g), and methylene chloride (250 ml) were placed in a 3L three-necked flask equipped with a mechanical stirrer and an addition funnel. The mixture was cooled to -10° to -15° C. and an ice-cold solution of bromine (53 ml, 1.04 moles) in 500 ml anhydrous methanol was added dropwise with stirring. Four hours after the addition of the bromine solution, the mixture was filtered by suction. The excess solvent was removed on a rotatory evaporator and the crude product was distilled under reduced pressure to give colorless 2-methoxymethyl-2,5-dimethoxy-2,5-dihydrofuran (118.3 g, 65%), bp. 57°-58° C. (0.2 mm Hg), n21 -1.4414.

Workup

  1. customequipped with a mechanical stirrer and an addition funnel
  2. temperatureThe mixture was cooled to -10° to -15° C.
  3. filtrationthe mixture was filtered by suction
  4. customThe excess solvent was removed on a rotatory evaporator
  5. distillationthe crude product was distilled under reduced pressure

Sources & evidence

ORD record
ord-59e0d86e17614949b2ed0ac8f7ec3c33
Source dataset
uspto-grants-1989_11
Patent number
US04883813

Reaction notes

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