Diethyl Ether → 1,1-Bis(2-methoxyphenyl)ethanol

HRID 359182Notes

Reaction equation

HRID 359182 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])=[O:6].[CH3:19]COCC.C[Mg]Br>O>[CH3:14][O:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:5]([C:4]1[CH:15]=[CH:16][CH:17]=[CH:18][C:3]=1[O:2][CH3:1])([OH:6])[CH3:19]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 5847282,2'-DimethoxybenzophenoneHCID 178418573HCID 178418573, compound

Product 1

HCID 144182001,1-Bis(2-methoxyphenyl)ethanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,2'-Dimethoxybenzophenone (24.2 g, 0.14 mole) and 400 ml of ether were placed in a 1 1 flask and stirred at ambient temperature and methyl magnesium bromide (40 ml of 3.0 M solution in ether) was added dropwise. The resulting mixture was stirred overnight and then a few ml of water were added to quench the Grignard reagent. About 300 ml of ethyl acetate and 250 ml of 10 percent hydrochloric acid were then added and the mixture was shaken. The organic layer was next recovered, extracted with 100 ml of water and 100 ml of saturated sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain 25.6 g (98 percent of theory) of the title compound as a white solid melting at 122°-123° C. The proton NMR spectrum was consistent with the assigned structure.

Workup

  1. stirringThe resulting mixture was stirred overnight
  2. customto quench the Grignard reagent
  3. additionAbout 300 ml of ethyl acetate and 250 ml of 10 percent hydrochloric acid were then added
  4. stirringthe mixture was shaken
  5. extractionextracted with 100 ml of water and 100 ml of saturated sodium bicarbonate
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-daf77504693f43358fc10464515f4acf
Source dataset
uspto-grants-1991_03
Patent number
US04999448

Reaction notes

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