Methyl methoxyacetate → 1,1-Bis(3-fluorophenyl)-2-methoxyethanol

HRID 1196239Notes

Reaction equation

HRID 1196239 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([Mg]Br)[CH:5]=[CH:6][CH:7]=1.[CH3:10][O:11][CH2:12][C:13]([O:15]C)=O>C1COCC1.C(O)=O>[F:1][C:2]1[CH:3]=[C:4]([C:13]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[CH:7]=2)([OH:15])[CH2:12][O:11][CH3:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 80507Methyl methoxyacetateHCID 178505773HCID 178505773, compound

Product 1

HCID 537223311,1-Bis(3-fluorophenyl)-2-methoxyethanol

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1,1-bis(3-fluorophenyl)-2-methoxyethanol (156.7 g) (obtained by the reaction of 3-fluorophenylmagnesium bromide with methyl 2-methoxyacetate in THF) in formic acid (160 cc) is heated to reflux for 16 hours, cooled and poured into a mixture of saturated sodium carbonate solution (800 cc) and ethyl acetate (500 cc). The organic phase is washed with water (2×500 cc) and with saturated sodium chloride solution (500 cc), then dried and concentrated to dryness under reduced pressure (2.7 kPa) to give bis(3-fluorophenyl)acetaldehyde (144.5 g) in the form of a yellow oil.

Sources & evidence

ORD record
ord-a0b20543a7974f958b8ba7820131daae
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

Loading…