3-Chloro-2-methoxymethoxy-2'-methoxymethoxybenzophenone → 1-(3-Chloro-2-methoxymethoxyphenyl)-1-(2-methoxymethoxyphenyl)ethene

HRID 359196Notes

Reaction equation

HRID 359196 reaction equation
C[Si](C[Li])(C)C.[Cl:7][C:8]1[C:9]([O:26][CH2:27][O:28][CH3:29])=[C:10]([CH:23]=[CH:24][CH:25]=1)[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH2:20][O:21][CH3:22])=O.[CH3:30]C(C)([O-])C.[K+]>CCCCC.O1CCCC1.CCOCC>[Cl:7][C:8]1[C:9]([O:26][CH2:27][O:28][CH3:29])=[C:10]([C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH2:20][O:21][CH3:22])=[CH2:30])[CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 3

HCID 198126723-Chloro-2-methoxymethoxy-2'-methoxymethoxybenzophenoneHCID 23665647Potassium tert-butoxideHCID 178418939HCID 178418939, compound2×

Product 1

HCID 198126591-(3-Chloro-2-methoxymethoxyphenyl)-1-(2-methoxymethoxyphenyl)etheneYield 230.5%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 1.0 M solution of trimethylsilylmethyl lithium in pentane (160 ml) was added with stirring to a solution of 50.5 g of 3-chloro-2-methoxymethoxy-2'-methoxymethoxybenzophenone in 500 ml of tetrahydrofuran over a 45 min period. There was a mild exotherm. Analysis by gas-liquid chromatography indicated the reaction was incomplete so another 10 ml of the trimethylsilylmethyl lithium solution was added. After a 20 min reaction period 7.3 g of potassium t-butoxide were added and the reaction was heated to reflux with a heating mantle and held there for 40 min. The mixture was then allowed to cool and was diluted with 1 1 of ether. The ethereal solution was extracted with 6-300 ml portions of water and 200 ml of brine, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain 50.2 g of the title compound as a pale orange oil. The proton NMR spectrum was consistent with the assigned structure.

Workup

  1. additionwas added
  2. additionwere added
  3. temperaturethe reaction was heated
  4. temperatureto reflux with a heating mantle
  5. temperatureto cool
  6. extractionThe ethereal solution was extracted with 6-300 ml portions of water and 200 ml of brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-198cd344d5534cf6abf3f7ac7f9917a4
Source dataset
uspto-grants-1991_03
Patent number
US04999448

Reaction notes

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