Tetrahydrofuran → 3-Benzyloxybenzene-2-propanol

HRID 649333Notes

Reaction equation

HRID 649333 reaction equation
C[Mg]I.[CH2:4]([O:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)C(OC)=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[O:22]1C[CH2:25][CH2:24][CH2:23]1>CCOCC>[CH2:4]([O:11][C:12]1[C:21]([CH2:25][CH2:24][CH2:23][OH:22])=[CH:20][CH:19]=[CH:14][CH:13]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 13368031Methyl 3-(benzyloxy)benzoateHCID 178418373HCID 178418373, compound

Product 1

HCID 189738553-Benzyloxybenzene-2-propanolYield 93%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a 0° solution of 2.2 mole of methyl magnesium iodide in 1.5 l. ether is added a solution of 200 g. (1.06 mole) of methyl 3-benzyloxybenzoate in 500 ml. ether and 500 ml. tetrahydrofuran. The reaction mixture is stirred for 3 hours and then added to 1.5 l. ice cold saturated ammonium chloride and 2 l. ether. The organic extract is dried over magnesium sulfate and evaporated to an oil. Crystallization of the crude oil in petroleum ether gives 186 g. (93%) of the title compound.

Workup

  1. customTo a 0°
  2. additionadded to 1.5 l
  3. extractionThe organic extract
  4. dry with materialis dried over magnesium sulfate
  5. customevaporated to an oil
  6. customCrystallization of the crude oil in petroleum ether
  7. customgives 186 g

Sources & evidence

ORD record
ord-4f3e509c72f04a328c0d519e9dfb6fc9
Source dataset
uspto-grants-1988_04
Patent number
US04739079

Reaction notes

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