methyl 2-ethoxyacetate → HCID 54202865, compound

HRID 1196252Notes

Reaction equation

HRID 1196252 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][CH:4]=[C:3]([Mg]Br)[CH:2]=1.C([O:12][CH2:13][C:14]([O:16][CH3:17])=O)C>O1CCCC1.C(O)=O>[C:1]1([CH3:9])[CH:6]=[CH:5][CH:4]=[C:3]([C:13]([C:3]2[CH:2]=[C:1]([CH3:9])[CH:6]=[CH:5][CH:4]=2)([OH:12])[CH2:14][O:16][CH3:17])[CH:2]=1

Participants

5

Reactant 2

HCID 325385methyl 2-ethoxyacetateHCID 178425413HCID 178425413, compound

Product 1

HCID 54202865HCID 54202865, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1,1-bis(3-tolyl)-2-methoxyethanol (24.66 g) (obtained by the reaction of 3-tolylmagnesium bromide with methyl 2-ethoxyacetate in tetrahydrofuran) in formic acid (30 cc) is heated to reflux for 12 hours, cooled and poured into a mixture of saturated sodium carbonate solution (400 cc) and ethyl acetate (400 cc). The organic phase is washed with water (3×300 cc) and with saturated sodium chloride solution (300 cc) then dried and concentrated to dryness under reduced pressure (2.7 kPa) to give bis(3-tolyl)acetaldehyde (20.45 g) in the form of a yellow oil.

Sources & evidence

ORD record
ord-073d8a43abbe4769943b12a5f164c9e9
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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