Acetic Acid → 2-(4-formylphenyl)acetic Acid
Reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.C1N2CN3CN(C2)CN1C3.C(O)(=[O:25])C.O>C(O)C>[CH:2]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1)=[O:25]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
The title compound was synthesized by referring to Org. Synth., 1963, IV, 690. A suspension of (4-bromomethylphenyl)acetic acid (6.0 g) and hexamethylenetetramine (11.1 g) in ethanol (80 ml) was stirred for 2 hours at 100° C., then acetic acid (20 ml) and water (20 ml) were sequentially added thereto followed by stirring for 1.5 hours at 100° C. The solvent was evaporated in vacuo, extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. A solution of the residue in tetrahydrofuran was filtered through silica gel, then the solvent was evaporated in vacuo, and the resulting solid was washed with a hexane-diethyl ether system to provide the title compound (2.0 g).
Workup
- customThe title compound was synthesized
- stirringby stirring for 1.5 hours at 100° C
- customThe solvent was evaporated in vacuo
- extractionextracted with ethyl acetate
- washsequentially washed with water and brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated in vacuo
- filtrationA solution of the residue in tetrahydrofuran was filtered through silica gel
- customthe solvent was evaporated in vacuo
- washthe resulting solid was washed with a hexane-diethyl ether system
Sources & evidence
- ORD record
- ord-aa9a57bad32e4ef8a4c93b5b1c5ffa7b
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399520B2
Reaction notes
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