Acetic Acid → Methyl 4-Formylbenzoate

HRID 223769Notes

Reaction equation

HRID 223769 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6](CBr)=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:4].C1N2CN3CN(C2)CN1C3.[C:23](O)(=[O:25])C.Cl>O>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:23]=[O:25])=[CH:7][CH:6]=1)([O:2][CH3:1])=[O:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 2734813Methyl 2-(bromomethyl)benzoate

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-α-bromotoluate, 84 g (0.6 mole) of hexamethylenetetraamine, 150 ml of acetic acid and 150 ml of water were refluxed with stirring for two hr. Ninety ml of concentrated hydrochloric acid was then added and kept at room temperature for 15 min. 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 ##STR6## 1690 cm-1 (--CHO). NMR (CDCl3) 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 min
  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-45cd70a1fc13454ca900f4bbd30d42ce
Source dataset
uspto-grants-1982_10
Patent number
US04356298

Reaction notes

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