Hydrochloric Acid → Ethyl 4-(phenylmethoxy)benzoate

HRID 1576922Notes

Reaction equation

HRID 1576922 reaction equation
C[Mg]I.[Mg].CI.BrC1C=CC([CH:14]([O:21][CH:22]([C:29]2[CH:34]=[CH:33][C:32](Br)=[CH:31][CH:30]=2)C2C=CC=CC=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17]C=2)=CC=1.Cl[C:37]([O:39][CH2:40][CH3:41])=[O:38].Cl>CCOCC.O>[CH2:40]([O:39][C:37]([C:19]1[CH:20]=[CH:15][C:14]([O:21][CH2:22][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[CH:17][CH:18]=1)=[O:38])[CH3:41]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 10928Ethyl chloroformateHCID 5462224MagnesiumHCID 155553134-Bromo-phenylbenzyl etherHCID 178418373HCID 178418373, compound

Product 1

HCID 191414Ethyl 4-(phenylmethoxy)benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

To a solution of methyl magnesium iodide prepared from magnesium (0.72g.; 0.03 mole) and methyl iodide (1.42g.; 0.01 mole) in ether (20ml) using standard methods, 4-bromo-phenylbenzyl ether in ether (20ml) was added dropwise with stirring then stirred until reaction was complete (1hr.). Ethyl chloroformate (3.24g.; 0.03 mole) in dry ether (20ml) was then added to the reaction mixture which was then boiled under reflux for 2 hrs. After cooling the reaction mixture was allowed to stand at room temperature for two days then worked up by the addition of water (40ml) and dilute hydrochloric acid (20ml). Separation of the ether layer followed by drying (anhyd. MgSO4), yielded 4-ethoxycarbonylphenoxy phenyl methane, m.p. 45°C.

Workup

  1. additionwas added dropwise
  2. stirringthen stirred until reaction
  3. custom(1hr.)
  4. temperatureunder reflux for 2 hrs
  5. temperatureAfter cooling the reaction mixture
  6. customSeparation of the ether layer
  7. dry with materialby drying (anhyd. MgSO4)

Sources & evidence

ORD record
ord-60e5c5bdc033454eb104033ced70cb48
Source dataset
uspto-grants-1976_09
Patent number
US03983164

Reaction notes

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