Acetic Acid → Methyl 4-Formylbenzoate

HRID 2198788Notes

Reaction equation

HRID 2198788 reaction equation
C[C:2]1[C:3](Br)=[C:4]([C:9]([O-:11])=[O:10])[C:5](C)=[CH:6][CH:7]=1.[CH2:13]1N2CN3CN(C2)CN1C3.[C:23](O)(=[O:25])C.Cl>O>[C:9]([C:4]1[CH:3]=[CH:2][C:7]([CH:23]=[O:25])=[CH:6][CH:5]=1)([O:11][CH3:13])=[O:10]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 86738633HCID 86738633, compound

Product 1

HCID 15294Methyl 4-FormylbenzoateYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 68.7 g (0.3 mole) of methyl- -bromotoluate, 84 g (0.6 mole) of hexamethylenetetramine, 150 ml of acetic acid and 150 ml of water were refluxed with stirring for two hours. Ninety ml of concentrated hydrochloric acid was then added and kept at room temperature for 15 minutes. The cooled solution was extracted with ether, washed with water, 10% NaHCO3 solution, water and dried. Evaporation of the solvent and recrystallization of the residue from petroleum ether gave 35 g of p-carbomethoxybenzaldehyde, yield 71% m.p. 61°-63° C. (lit. m.p. 61°-63° C.). The infrared spectrum showed absorption at 1720 cm-1 ##STR9## 1690 cm-1 (--CHO). NMR (CDCI3) δ3.8 (s, --COOCH3, 3), 7.8-8.2 (m, aromatic, 4), and 10.2 (s, --CHO, 1).

Workup

  1. temperaturewere refluxed
  2. waitkept at room temperature for 15 minutes
  3. extractionThe cooled solution was extracted with ether
  4. washwashed with water, 10% NaHCO3 solution, water
  5. customdried
  6. customEvaporation of the solvent and recrystallization of the residue from petroleum ether

Sources & evidence

ORD record
ord-3fa756dc5eca4308b1eccdaab9056bed
Source dataset
uspto-grants-1982_11
Patent number
US04359568

Reaction notes

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