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Dichloromethane → HCID 19900861, compound

HRID 1029708
Notes
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Reaction equation

HRID 1029708 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 24408Bromine2×HCID 61661Furfuryl methyl ether

Product 1

HCID 19900861HCID 19900861, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887Methanol
Solvent
2×

Conditions

Temperature
-12.5 °C

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-2,5dihydrofuran (118.3 g, 65%), bp. 57°-58° C. (0.2 mm Hg), nD =1.4414.

Workup

  1. customequipped with a mechanical stirrer and an addition funnel
  2. filtrationthe mixture was filtered by suction
  3. customThe excess solvent was removed on a rotatory evaporator
  4. distillationthe crude product was distilled under reduced pressure

Sources & evidence

ORD record
ord-8cdb88a1c3114f07a031836cf74be15c
Source dataset
uspto-grants-1992_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05102909

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes