Methane, dichloromethoxy- → HCID 19047071, compound

HRID 1780603Notes

Reaction equation

HRID 1780603 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][C:8]([CH3:12])([CH3:11])[CH2:7][C:6]=2[C:5]([CH3:13])=[C:4]([CH3:14])[CH:3]=1.[CH3:15][O:16]C(Cl)Cl>ClCCl>[Cl:1][C:2]1[C:10]2[O:9][C:8]([CH3:11])([CH3:12])[CH2:7][C:6]=2[C:5]([CH3:13])=[C:4]([CH3:14])[C:3]=1[CH:15]=[O:16]

Participants

4

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 152683107-Chloro-2,2,4,5-tetramethyl-2,3-dihydro-1-benzofuran

Product 1

HCID 19047071HCID 19047071, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 20 g of the 7-chloro-2,3-dihydro-2,2,4,5-tetramethylbenzofuran in 200 ml of absolute dichloromethane was added 27.3 ml of titanium chloride(IV) and 18.75 ml of α,α-dichloromethyl methyl ether at 0° C. With stirring at room temperature for 45 minutes and refluxing for 15 minutes, the reaction mixture was quenched with 200 ml of ice-water and stirred for 30 minutes and the aqueous layer was extracted with dichloromethane. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford a crude product. Final purification was carried by silica-gel column chromatography to afford 14 g of 7-chloro-2,3-dihydro-2,2,4,5-tetramethylbenzofuran-6-carboxaldehyde.

Workup

  1. temperaturerefluxing for 15 minutes
  2. customthe reaction mixture was quenched with 200 ml of ice-water
  3. stirringstirred for 30 minutes
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto afford a crude product
  9. customFinal purification

Sources & evidence

ORD record
ord-04710dabf252488eba97a1fe166df50e
Source dataset
uspto-grants-1997_05
Patent number
US05631208

Reaction notes

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