Ethanol → Methyl 4-(3-formylphenyl)benzoate

HRID 1860011Notes

Reaction equation

[CH:1]([C:3]1[CH:4]=[C:5](OB(O)O)[CH:6]=[CH:7][CH:8]=1)=[O:2].C[C:14]1[CH:22]=[C:21](Br)[CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17].[CH2:24](O)C.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:1]([C:3]1[CH:4]=[C:5]([C:21]2[CH:20]=[CH:19][C:15]([C:16]([O:18][CH3:24])=[O:17])=[CH:14][CH:22]=2)[CH:6]=[CH:7][CH:8]=1)=[O:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of tetrakis(triphenylphosphine)palladium (297 mg) was added to a solution of 3-formylphenylboric acid (3.00 g) and methyl 4-bromobenzoic acid (4.30 g) in a mixture of toluene (30 ml), ethanol (50 ml) and saturated aqueous sodium hydrogencarbonate solution (30 ml) at ambient temperature. The mixture was heated at reflux for 2 hours at 100° C. The reaction mixture was partitioned between ethyl acetate and water and the layers were separated. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from diisopropyl ether to afford the title compound (3.37 g) as colorless crystals.

Workup

temperatureThe mixture was heated
customThe reaction mixture was partitioned between ethyl acetate and water
customthe layers were separated
washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record: ord-1bda2d917f2f471eb1211d82bf09e522
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528525B1

Reaction notes

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