Water → Methyl 2-(2-chloromethyl-5-methylphenoxy)propionate

HRID 257351Notes

Reaction equation

HRID 257351 reaction equation
O[CH2:2][C:3]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:4]=1[O:5][CH:6]([CH3:11])[C:7]([O:9][CH3:10])=[O:8].S(Cl)([Cl:19])=O.O>C(Cl)Cl.N1C=CC=CC=1>[Cl:19][CH2:2][C:3]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:4]=1[O:5][CH:6]([CH3:11])[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 23286418Methyl 2-(2-hydroxymethyl-5-methylphenoxy)propionate

Product 1

HCID 15765398Methyl 2-(2-chloromethyl-5-methylphenoxy)propionate

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.20 g (0.0098 mole) of methyl 2-(2-hydroxymethyl-5-methylphenoxy)propionate in 10 mL of dry methylene chloride was added to a colorless solution of 1.28 g (0.0108 mole) of thionyl chloride and 5 drops of pyridine in 10 mL of dry methylene chloride during a 10 minute period. This mixture was heated at reflux for one hour and then poured into 50 mL of water. The phases were separated, and the aqueous phase was extracted three times with methylene chloride. These extracts were combined with the organic phase, which was then washed three times with a saturated aqueous solution of sodium bicarbonate and once with a saturated aqueous solution of sodium chloride. The organic phase was then dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated under reduced pressure, leaving a yellow oil as a residue. This oil was placed on a silica gel column and eluted with methylene chloride. After the product-containing fractions were combined and the solvent evaporated under reduced pressure, 2.06 g of methyl 2-(2-chloromethyl-5-methylphenoxy)propionate was recovered as a colorless oil. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureThis mixture was heated
  2. temperatureat reflux for one hour
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted three times with methylene chloride
  5. washwas then washed three times with a saturated aqueous solution of sodium bicarbonate
  6. dry with materialThe organic phase was then dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate was evaporated under reduced pressure
  9. customleaving a yellow oil as a residue
  10. washeluted with methylene chloride
  11. customthe solvent evaporated under reduced pressure, 2.06 g of methyl 2-(2-chloromethyl-5-methylphenoxy)propionate
  12. customwas recovered as a colorless oil

Sources & evidence

ORD record
ord-fe96108ecf36480db703e519f1065374
Source dataset
uspto-grants-1993_11
Patent number
US05262390

Reaction notes

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