Sodium Hydroxide → 3-(3-Benzyloxyphenyl)-1-butanol

HRID 261352Notes

Reaction equation

HRID 261352 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11](/[C:15](/[CH3:22])=[CH:16]\[C:17](OCC)=[O:18])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[OH-].[Na+]>CCOCC.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]([CH3:22])[CH2:16][CH2:17][OH:18])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 70527588Ethyl 3-(3-Benzyloxyphenyl)crotonate

Product 1

HCID 147426233-(3-Benzyloxyphenyl)-1-butanol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of ethyl 3-(3-benzyloxyphenyl)crotonate (17.7 g., 60 mM) in ether (250 ml.) is added to a mixture of lithium aluminum hydride (3.42 g., 90 mM) and ether (250 ml.). Aluminum chloride (0.18 g., 1.35 mM) is added and the mixture refluxed for 12 hours and then cooled. Water (3.4 ml.), sodium hydroxide (3.4 ml. of 6 N) and water (10 ml.) are then added successively to the reaction mixture. The inorganic salts which precipitate are filtered off and the filtrate is then concentrated in vacuo to give the desired alcohol as an oil.

Workup

  1. temperaturethe mixture refluxed for 12 hours
  2. temperaturecooled
  3. filtrationThe inorganic salts which precipitate are filtered off
  4. concentrationthe filtrate is then concentrated in vacuo

Sources & evidence

ORD record
ord-e5ce4b61b0524cfaa68e63aa3c42b4c5
Source dataset
uspto-grants-1979_08
Patent number
US04165323

Reaction notes

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