Methane, dichloromethoxy- → HCID 19855493, compound

HRID 2227095Notes

Reaction equation

HRID 2227095 reaction equation
[CH2:1]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH3:19][O:20]C(Cl)Cl>[Ti](Cl)(Cl)(Cl)Cl.ClCCl>[CH2:1]([C:13]1[CH:14]=[CH:15][C:16]([CH:19]=[O:20])=[CH:17][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 31237Dodecylbenzene

Product 1

HCID 19855493HCID 19855493, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To 70 mL of dehydrated dichloromethane, 24.68 g (100 mmol) of n-dodecylbenzene was added and 36.82 g (189 mmol) of titanium tetrachloride was gradually added in drops. The reaction system kept below 10° C. in an ice bath and 13.16 9 (114 mmol) of 1,1-dichloromethl methy ether added in drops thereto were stirred together below 10° C. for 30 minutes and further stirred at a room temperature for 45 minutes. The resultant reaction mixture was added to 500 mL of ice water. It was extracted four times with 200 mL of dichloromethane and dried overnight on sodium sulfate. The solvent was removed by the use of an evaporator and purified by column chromatography (silica gel, benzene:hexene =1:1). Consequently, 11.22 g (40.2 mmol) of a light yellow slightly viscous liquid was obtained. The yield was 40%.

Workup

  1. customThe reaction system kept below 10° C. in an ice bath
  2. stirringfurther stirred at a room temperature for 45 minutes
  3. customThe resultant reaction mixture
  4. extractionIt was extracted four times with 200 mL of dichloromethane
  5. customdried overnight on sodium sulfate
  6. customThe solvent was removed by the use of an evaporator
  7. custompurified by column chromatography (silica gel, benzene:hexene =1:1)
  8. customConsequently, 11.22 g (40.2 mmol) of a light yellow slightly viscous liquid was obtained

Sources & evidence

ORD record
ord-6a975dac1ff14d6da6746883679d4cec
Source dataset
uspto-grants-2002_07
Patent number
US06413447B1

Reaction notes

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