Hydrochloric Acid → Benzyl Phenyl Ether

HRID 728519Notes

Reaction equation

HRID 728519 reaction equation
[Mg].II.[CH2:4]([O:11][C:12]1[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C[C@@H](CCCC(C)C)C=O.Cl.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:4]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 807IodineHCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 516892Sodium BicarbonateHCID 5462224Magnesium2×HCID 14139287HCID 14139287, compound

Product 1

HCID 70352Benzyl Phenyl EtherYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

In a 200 ml-volume flask was charged 1 704 g of metallic magnesium. After displacing the atmosphere with nitrogen, a small amount of iodine was added thereto, followed by heating to activate the magnesium. Ten milliliters of tetrahydrofuran (THF) were added thereto, and a mixture comprising 18.5 g of 4-bromophenyl benzyl ether as prepared in Example 1 and 40 ml of THF was added dropwise to the system from a dropping funnel at room temperature over a period of 30 minutes. The reaction was continued at a refluxing temperature of THF for an additional 2.5 hours to prepare a Grignard reagent. To the resulting Grignard reagent was added a mixture of 10.0 g of (S)-2,6-dimethylheptanal and 30 ml of THF at 15° C., followed by allowing the mixture to react for 2 hours while keeping at that temperature. The reaction mixture was treated with diluted hydrochloric acid, neutralized with a sodium bicarbonate aqueous solution, and washed with water to obtain 21.8 g of a crude product. Purification by silica gel column chromatography (eluent: benzene) yielded 11.8 g (theoretical yield: 47%) of the entitled compound as a viscous yellow liquid.

Workup

  1. temperatureby heating
  2. additionwas added dropwise to the system from a dropping funnel at room temperature over a period of 30 minutes
  3. customto react for 2 hours
  4. washwashed with water
  5. customto obtain 21.8 g of a crude product
  6. customPurification by silica gel column chromatography (eluent: benzene)

Sources & evidence

ORD record
ord-3b76e8062ca7487c974a0f043b1d7cf6
Source dataset
uspto-grants-1991_09
Patent number
US05049308

Reaction notes

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