Methanol → 1,1-Diphenyl-10-undecen-1-ol

HRID 275464Notes

Reaction equation

HRID 275464 reaction equation
[C:1]([O:13]CC)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].[C:16]1([Mg]Br)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CO>C1COCC1>[C:16]1([C:1]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([OH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 12729Ethyl 10-undecenoateHCID 178418255HCID 178418255, compound

Product 1

HCID 200883261,1-Diphenyl-10-undecen-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 10.6 g of ethyl undecylenate in 100 mL of THF at 0° C. was added, over 1 hr, 40 mL of 3M phenyl magnesium bromide. The mixture was warmed to room temperature and stirred for 75 hrs. Methanol, 10 mL, was added to quench the excess Grinard reagent and the solvent was distilled in vacuo. The residue was shaken with diethyl ether and dilute hydrochloric acid. The ether layer was washed with water and saturated sodium hydrogen carbonate, dried, and concentrated in vacuo to give 18.3 g of crude product, which was then chromatographed on silica gel with chloroform as the eluent, to give 13.7 g of 1,1-diphenyl-10-undecen-1-ol which is characterized by:

Workup

  1. customto quench the excess Grinard reagent
  2. distillationthe solvent was distilled in vacuo
  3. stirringThe residue was shaken with diethyl ether and dilute hydrochloric acid
  4. washThe ether layer was washed with water and saturated sodium hydrogen carbonate
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customto give 18.3 g of crude product, which
  8. customwas then chromatographed on silica gel with chloroform as the eluent

Sources & evidence

ORD record
ord-6cb8f2f55a024083988d5d0bfd71aa31
Source dataset
uspto-grants-1995_02
Patent number
US05393795

Reaction notes

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