Benzophenone → HCID 11020538, compound

HRID 275469Notes

Reaction equation

HRID 275469 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([Mg]Cl)[CH:16]=[CH2:17]>O1CCCC1>[C:2]1([C:1]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)([OH:8])[CH2:17][CH:16]=[CH2:15])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3102BenzophenoneHCID 178418473HCID 178418473, compound

Product 1

HCID 11020538HCID 11020538, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 29 g of benzophenone in 150 mL of tetrahydrofuran (THF) at 0° C. was added 88 mL of 2M allyl magnesium chloride. After 16 hrs, the starting material was completely consumed as indicated by thin layer chromatography (TLC). To the reaction mixture was added 1 mL of methanol to quench the excess Grinard reagent. The THF was distilled in vacuo and the residue was shaken with dilute aqueous hydrochloric acid and chloroform. The layers were separated and the aqueous phase was extracted with chloroform. The combined organic layers were dried with sodium sulfate and concentrated in vacuo to give 37 g of 1,1-diphenyl-3-buten-1-ol which is characterized by:

Workup

  1. customthe starting material was completely consumed
  2. additionTo the reaction mixture was added 1 mL of methanol
  3. customto quench the excess Grinard reagent
  4. distillationThe THF was distilled in vacuo
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted with chloroform
  7. dry with materialThe combined organic layers were dried with sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-41b6671d0e64475c88cf94502ba37d07
Source dataset
uspto-grants-1995_02
Patent number
US05393797

Reaction notes

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