Methyl methoxyacetate → HCID 54243492, compound

HRID 1196247Notes

Reaction equation

HRID 1196247 reaction equation
[Cl: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>[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([Cl: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 178478127HCID 178478127, compound

Product 1

HCID 54243492HCID 54243492, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1,1-bis(3-chlorophenyl)-2-methoxyethanol (47 g) (obtained by the reaction of 3-chlorophenylmagnesium bromide with methyl 2-methoxyacetate in THF) in formic acid (44 cc) is heated to reflux for 5 hours, cooled and poured into a mixture of saturated sodium carbonate solution (500 cc) and ethyl acetate (300 cc). The organic phase is washed with water (3×250 cc) and with saturated sodium chloride solution (200 cc), then dried and concentrated to dryness under reduced pressure (2.7 kPa) to give bis(3-chlorophenyl)acetaldehyde (36.9 g) in the form of a yellow oil.

Sources & evidence

ORD record
ord-c8ab7622acdf431189ad16ee7b21d7e2
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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