Benzophenone → 1,1-Diphenyl-5-methoxy-1-pentanol

HRID 1981329Notes

Reaction equation

HRID 1981329 reaction equation
[Mg].Br[CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH3:8].[C:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CCOCC>[C:17]1([C:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)([OH:16])[CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH3:8])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 3102BenzophenoneHCID 5211681-Bromo-4-methoxybutaneHCID 5462224Magnesium

Product 1

HCID 131250861,1-Diphenyl-5-methoxy-1-pentanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a suspension of 3.9 g. (0.16 mole) of magnesium turnings in 300 ml. of dry ether was added dropwise 26.7 g. (0.16 mole) of 1-bromo-4-methoxybutane in 80 ml. of ether and the mixture refluxed for four hours. The reaction mixture was cooled and 14.6 g. (0.008 mole) of benzophenone in 100 ml. of dry ether was added dropwise. The mixture was stirred at ambient temperature for 18 hours, cautiously quenched with water and the ether layer separated. The aqueous layer was extracted with ether and the combined ether extract was dried and concentrated to give 1,1-diphenyl-5-methoxy-1-pentanol, m.p. 112°-115° C.

Workup

  1. additionTo a suspension of 3.9 g
  2. temperatureThe reaction mixture was cooled
  3. customcautiously quenched with water
  4. customthe ether layer separated
  5. extractionThe aqueous layer was extracted with ether
  6. extractionthe combined ether extract
  7. customwas dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-bdd4eca246e54fecbee108b1af92ab68
Source dataset
uspto-grants-1985_04
Patent number
US04514414

Reaction notes

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