Water → Benzoic acid, 3-formyl-4-hydroxy-, methyl ester
Reaction equation
FC(F)(F)[C:3](O)=[O:4].O[C:9]1([CH:18]=[CH:17][CH:16]=[CH:15][CH2:14]1)[C:10]([O:12][CH3:13])=[O:11].C1N2CN3CN(C2)CN1C3.[OH2:29]>>[CH:3]([C:15]1[CH:14]=[C:9]([CH:18]=[CH:17][C:16]=1[OH:29])[C:10]([O:12][CH3:13])=[O:11])=[O:4]Participants
Procedure
24 ml of trifluoroacetic acid are added at 0° C. to a mixture of 4.56 g (30 mmol) of methyl 1-hydroxybenzoate and 8.64 g (60 mmol) of hexamethylenetetramine. The solution is brought to reflux and is stirred for 2 hours. After cooling, the solution is diluted with water to 50 ml. The solution is stirred overnight at ambient temperature and is then extracted with ether. The combined organic phases are then washed with water and then with brine. After drying over sodium sulfate and concentrating under vacuum, the crude reaction product is purified by chromatography on silica gel (ethyl acetate/heptane 10/90) to give 2 g (37%) of methyl 3-formyl-4-hydroxybenzoate in the form of a white solid; 1H NMR (300 MHz, CDCl3): 11.30 (broad s, 1H), 9.90 (s, 1H), 8.26 (d, J=2.1 Hz, 1H), 8.12 (dd, J=2.1 Hz and 8.7 Hz, 1H), 6.96 (d, J=8.7 Hz, 1H), 3.88 (s, 3H).
Workup
- temperatureto reflux
- temperatureAfter cooling
- stirringThe solution is stirred overnight at ambient temperature
- extractionis then extracted with ether
- washThe combined organic phases are then washed with water
- dry with materialAfter drying over sodium sulfate
- concentrationconcentrating under vacuum
- customthe crude reaction product
- customis purified by chromatography on silica gel (ethyl acetate/heptane 10/90)
Sources & evidence
- ORD record
- ord-da6893c26e3d4b92944c5b272507bc23
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07071340B2
Reaction notes
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