Bis(Chloromethyl) Ether → HCID 53877441, compound

HRID 1248351Notes

Reaction equation

HRID 1248351 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:8]2[CH:9]=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4].[CH2:15](Cl)[O:16]CCl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:8]2[CH:9]=[C:10]([O:13][CH3:14])[C:11]([CH:15]=[O:16])=[CH:12][C:7]=2[CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 10967Bis(Chloromethyl) EtherHCID 541184135-Methoxybenzocyclobutene-1-carboxylic acid methyl ester

Product 1

HCID 53877441HCID 53877441, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

3.84 g of 5-methoxybenzocyclobutene-1-carboxylic acid methyl ester are dissolved in 20 ml of dichloromethane, the whole is cooled to 0° and there are added dropwise thereto at from 0° to 5° firstly 3.16 g of titanium tetrachloride over a period of 3 minutes and then 3.83 g of dichlorodimethyl ether (Cl2CHOCH3) over a period of 20 minutes. The whole is then stirred for 5 minutes at from 0° to 5°, gradually heated to room temperature and then stirred for 15 minutes at 35°. The mixture is then left to cool to room temperature and poured onto 25 g of ice; the organic phase is separated off, the aqueous phase is then shaken three times with 10 ml of dichloromethane each time and the organic phases are combined, washed three times with 15 ml of ice-water each time, dried over magnesium sulphate, concentrated to dryness by evaporation and chromatographed over silica gel using dichloromethane as eluant. 4-formyl-5-methoxybenzocyclobutene-1-carboxylic acid methyl ester is obtained in the form of a colourless oil.

Workup

  1. temperaturethe whole is cooled to 0°
  2. additionthere are added dropwise
  3. stirringstirred for 15 minutes at 35°
  4. waitThe mixture is then left
  5. temperatureto cool to room temperature
  6. customthe organic phase is separated off
  7. stirringthe aqueous phase is then shaken three times with 10 ml of dichloromethane each time
  8. washwashed three times with 15 ml of ice-water each time
  9. dry with materialdried over magnesium sulphate
  10. concentrationconcentrated to dryness by evaporation
  11. customchromatographed over silica gel

Sources & evidence

ORD record
ord-ad10485e87644623a20f7615e34a204c
Source dataset
uspto-grants-1985_06
Patent number
US04523030

Reaction notes

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