(2-Phenylethoxy)acetic acid → 2-(2-Phenylethoxy)ethanol

HRID 1905963Notes

Reaction equation

HRID 1905963 reaction equation
[C:1]1([CH2:7][CH2:8][O:9][CH2:10][C:11](O)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:1]1([CH2:7][CH2:8][O:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 13208922(2-Phenylethoxy)acetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 132089292-(2-Phenylethoxy)ethanolYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

() The 2-phenylethoxyacetic acid obtained according to the preceding paragraph was dissoled in 50 ml of tetrahydrofuran and the solution was added dropwise over a period of 10 minutes to a stirred suspension, cooled in an ice-bath, of 1.62 g of lithium aluminum hydride in 50 ml of tetrahydrofuran. The mixture was stirred at room temperature for 0.5 hour. The excess lithium aluminum hydride was destroyed by the addition of 1.6 ml of water, then 1.6 ml of 15% aqueous sodium hydroxide solution and finally 5 ml of water. The inorganic solids were removed by filtration, washed well with diethyl ether and the filtrates were evaporated to give 6.50 g (92%) of 2-(2-phenylethoxy)ethanol in the form of an oil which was homogenous according to chromatography. This product can be distilled under reduced pressure; boiling point 140°-142° C./15 mm Hg.

Workup

  1. additionthe solution was added dropwise over a period of 10 minutes to a stirred suspension
  2. customThe excess lithium aluminum hydride was destroyed by the addition of 1.6 ml of water
  3. customThe inorganic solids were removed by filtration
  4. washwashed well with diethyl ether
  5. customthe filtrates were evaporated

Sources & evidence

ORD record
ord-077a330f9afd4fcc84dd14ebe8f62ade
Source dataset
uspto-grants-1987_03
Patent number
US04649160

Reaction notes

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