Methane, dichloromethoxy- → HCID 21435446, compound

HRID 2245903Notes

Reaction equation

HRID 2245903 reaction equation
[CH3:1][O:2]C(Cl)Cl.[Sn](Cl)(Cl)(Cl)Cl.[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][CH3:26])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[Ca+2].[Cl-]>ClCCCl.CCCCCC>[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([CH:1]=[O:2])=[CH:21][C:20]=1[CH2:25][CH3:26])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 21004Methane, dichloromethoxy-HCID 24287Tin tetrachlorideHCID 3461331-benzyloxy-2-ethylbenzeneHCID 5284359Calcium Chloride

Product 1

HCID 21435446HCID 21435446, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 8058HexaneSolvent

Procedure

In 25 g of 1,2-dichloroethane was dissolved 3.25 g (28 mmol) of dichloromethyl methyl ether, and the solution was chilled with ice-water. Here was added dropwise 7.36 g (28 mmol) of anhydrous tin (IV) chloride, and the mixture was stirred for 10 minutes. Here was added dropwise 5.00 g (23.55 mmol) of 1-benzyloxy-2-ethylbenzene obtained in Step 2 dissolved in 1,2-dichloroethane, and the mixture was stirred at ambient temperature for 5 hours. To the reaction mixture, aqueous solution of calcium chloride was added dropwise at 20° C. or below, 15 g of hexane was added, the organic layer was washed with water, and the solvent was evaporated. The residue was purified by column chromatography (ethyl acetate:hexane=1:10, SiO2) to yield the desired product, 4-benzyloxy-3-ethylbenzaldehyde, as yellow liquid (3.17 g, Yield: 56%).

Workup

  1. stirringthe mixture was stirred at ambient temperature for 5 hours
  2. washthe organic layer was washed with water
  3. customthe solvent was evaporated
  4. customThe residue was purified by column chromatography (ethyl acetate:hexane=1:10, SiO2)

Sources & evidence

ORD record
ord-76034a5763a841308afed8d85352f74a
Source dataset
uspto-grants-2010_03
Patent number
US07683203B2

Reaction notes

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