Water → 3-(Phenylmethoxy)benzenepropanol

HRID 322304Notes

Reaction equation

HRID 322304 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:19]=[CH:20][CH:21]=1)[CH:12]=[CH:13][C:14](OCC)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:12][CH2:13][CH2:14][OH:15])[CH:19]=[CH:20][CH:21]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 53965548Ethyl 3-benzyloxycinnamate

Product 1

HCID 126481553-(Phenylmethoxy)benzenepropanolYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 3-benzyloxycinnamate in tetrahydrofuran (300 ml) was added dropwise to a suspension of lithium aluminum hydride in tetrahydrofuran (300 ml) at 0° C. and then stirred for 2 hours. To the reaction mixture was added carefully water and the insoluble material was filtered off. The filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with 1N-hydrochloric acid and water, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography. From the fraction eluted with ethyl acetate-hexane (1:4, v/v), 3-(3-benzyloxyphenyl)propanol (52.7 g, 62%) was obtained. Oily substance.

Workup

  1. filtrationthe insoluble material was filtered off
  2. concentrationThe filtrate was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with 1N-hydrochloric acid and water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. washFrom the fraction eluted with ethyl acetate-hexane (1:4, v/v)

Sources & evidence

ORD record
ord-07b612656ae547299e07b8fce8c4720a
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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