Hydrochloric Acid → Propyl p-methoxybenzoate

HRID 2163657Notes

Reaction equation

HRID 2163657 reaction equation
[C:1](Cl)(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.C([OH:15])CC.Cl.N1C=C[CH:20]=[CH:19][CH:18]=1>>[C:1]([O:10][CH2:18][CH2:19][CH3:20])(=[O:15])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 10311-PropanolHCID 1049PyridineHCID 7477p-Anisoyl chloride

Product 1

HCID 243787Propyl p-methoxybenzoate

Conditions

Temperature
110 °C

Procedure

230 gm (1.32 mol) of anisoyl chloride were added drop by drop under agitation and cooling to a mixture of 316 gm (5.28 mol) of n-propanol and 300 ml of pyridine. The mixture was subsequently heated to 110° C. for three hours and then poured into a mixture of ice/water. The product was neutralized under cooling with half concentrated hydrochloric acid and extracted with ether. After drying, the ether phase was evaporated and the residue was fractionally distilled. The n-propyl anisate obtained had the following values:

Workup

  1. extractionextracted with ether
  2. customAfter drying
  3. customthe ether phase was evaporated
  4. distillationthe residue was fractionally distilled

Sources & evidence

ORD record
ord-635149d8d4e44d72905168f0e54de0bf
Source dataset
uspto-grants-1979_01
Patent number
US04136165

Reaction notes

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