O-Xylene → 4-Chloromethylbenzoicacid-(2,4-dichloro-6-methylphenyl) ester

HRID 443609Notes

Reaction equation

HRID 443609 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].C1(C)C(C)=CC=CC=1.[Cl:19][CH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[O:10][C:25](=[O:26])[C:24]1[CH:28]=[CH:29][C:21]([CH2:20][Cl:19])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 152922,4-Dichloro-6-methylphenolHCID 701364-(Chloromethyl)benzoyl chloride

Product 1

HCID 537543654-Chloromethylbenzoicacid-(2,4-dichloro-6-methylphenyl) ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

88.5 g (0.5 mole) of 2,4-dichloro-6-methylphenol, 180 ml of dry xylene, 95 g (0.5 mole) of p-chloromethylbenzoyl chloride and 0.5 ml of pyridine were refluxed for 24 hours in a weak current of nitrogen with the exclusion of moisture. After cooling, the slightly turbid (pyridine hydrochloride), orange-colored solution was filtered free of a small amount of a blackish brown resin, and the filtrate was freed of xylene at diminished pressure. The residue (165 g=100%) crystallized after two days of standing to a light brown crystal mass, which was triturated in 200 ml of ice-cold petroleum ether and suction filtered. After drying, nearly colorless crystals were obtained with a melting point of 71°-73° C. Recrystallization from petroleum ether (1:10) yielded white needles melting at 74°-75° C.; no change in the melting point was brought about by repeated recrystallization.

Workup

  1. temperatureAfter cooling
  2. filtrationthe slightly turbid (pyridine hydrochloride), orange-colored solution was filtered free of a small amount of a blackish brown resin
  3. customThe residue (165 g=100%) crystallized after two days
  4. customwas triturated in 200 ml of ice-cold petroleum ether
  5. filtrationsuction filtered
  6. customAfter drying
  7. customnearly colorless crystals were obtained with a melting point of 71°-73° C
  8. customRecrystallization from petroleum ether (1:10)

Sources & evidence

ORD record
ord-03f68a8ce47c4dd39baa4b629a8a1a93
Source dataset
uspto-grants-1981_04
Patent number
US04260803

Reaction notes

Loading…