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

HRID 225188Notes

Reaction equation

HRID 225188 reaction equation
C(O[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=1)(=O)/C=C/C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[OH-:31].[Na+]>CCOCC.O>[CH2:14]([O:13][C:9]1[CH:8]=[C:7]([CH:7]([CH3:12])[CH2:8][CH2:9][OH:31])[CH:12]=[CH:11][CH:10]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 131711957HCID 131711957, compound

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-7573b230fc164aadb377777aff6033ca
Source dataset
uspto-grants-1980_11
Patent number
US04235913

Reaction notes

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