Hydrochloric Acid → Ethyl 4-(phenylmethoxy)benzoate

HRID 866383Notes

Reaction equation

HRID 866383 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 15555313HCID 15555313, compoundHCID 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-f43de0a0470647e9b7c84bd43f0c06de
Source dataset
uspto-grants-1978_07
Patent number
US04098816

Reaction notes

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