Benzyl Alcohol → Ethyl 4-(phenylmethoxy)benzoate

HRID 1576925Notes

Reaction equation

HRID 1576925 reaction equation
[CH2:1](O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:11]=1.P(Cl)(Cl)(Cl)(Cl)Cl.O>CCOCC>[CH2:17]([O:16][C:14]([C:13]1[CH:12]=[CH:11][C:10]([O:9][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:20][CH:19]=1)=[O:15])[CH3:18]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 8434EthylparabenHCID 24819Phosphorus pentachloride

Product 1

HCID 191414Ethyl 4-(phenylmethoxy)benzoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Benzyl alcohol (2.70g.; 0.025 mole) was added to a solution of ethyl 4-hydroxybenzoate (4.15g.; 0.025 mole) in dry ether followed by the careful addition of phosphorus pentachloride (2.5g). The mixture was boiled under reflux for 24 hrs. then poured into water and the ether layer removed. The aqueous solution was extracted with ether and the combined organic extracts dried (anhyd. MgSO4) to yield, on evaporation and purification by chromatography, 4-ethoxycarbonylphenoxy phenyl methane, m.p. 45°C.

Workup

  1. temperatureunder reflux for 24 hrs
  2. customthe ether layer removed
  3. extractionThe aqueous solution was extracted with ether
  4. dry with materialthe combined organic extracts dried (anhyd. MgSO4)

Sources & evidence

ORD record
ord-16f3dba4843644488a7ad24f9ce7d21f
Source dataset
uspto-grants-1976_09
Patent number
US03983164

Reaction notes

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