Water → 1-(3-Chloro-2-methoxymethoxyphenyl)-1-(2-methoxyphenyl)ethanol

HRID 359190

Reaction equation

HRID 359190 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][O:10][CH3:11].[CH2:12]([Li])[CH2:13][CH2:14][CH3:15].[CH3:17][O:18][CH2:19][C:20]([C:22]1C=CC=C[CH:23]=1)=O.[OH2:28]>CCCCCC.O1CCCC1.CCOCC>[Cl:1][C:2]1[C:3]([O:8][CH2:9][O:10][CH3:11])=[C:4]([C:14]([C:13]2[CH:12]=[CH:23][CH:22]=[CH:20][C:19]=2[O:18][CH3:17])([OH:28])[CH3:15])[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 962WaterHCID 776982-Methoxy-1-phenylethanoneHCID 5426241-Chloro-2-(methoxymethoxy)benzeneHCID 178418339Butyllithium

Product 1

HCID 198126791-(3-Chloro-2-methoxymethoxyphenyl)-1-(2-methoxyphenyl)ethanol

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

1-Chloro-2-methoxymethoxybenzene (20.0 g) was combined with 72.5 ml of 1.6 M n-butyl lithium in hexane at 0° C. with stirring and allowed to react for 4 hours. A solution of 16.0 ml of 2-methoxyacetophenone in 20 ml of tetrahydrofuran was then added with stirring. After a short reaction period, water and ether were added and the ether layer was dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain an oil. This was purified by liquid chromatography, eluting with a 95:5 mixture of hexane and ethyl acetate, to obtain 6.67 g of the title compound as an oil. The assigned structure was consistent with the proton NMR spectrum.

Workup

  1. customto react for 4 hours
  2. stirringwith stirring
  3. additionwere added
  4. dry with materialthe ether layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customto obtain an oil
  8. customThis was purified by liquid chromatography
  9. washeluting with a 95:5 mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-20f35688785146699d63a7c3bac505d9
Source dataset
uspto-grants-1991_03
Patent number
US04999448

Linked notes

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