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Water → 2-(3,4,5-Trimethoxyphenyl)benzyl Alcohol

HRID 1634867
Notes
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Reaction equation

HRID 1634867 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:23]=[CH:22][CH:21]=[CH:20][C:14]=2[C:15](OCC)=[O:16])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:13]2[CH:23]=[CH:22][CH:21]=[CH:20][C:14]=2[CH2:15][OH:16])[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 22558004Ethyl 2-(3,4,5-trimethoxyphenyl)benzoate

Product 1

HCID 213388232-(3,4,5-Trimethoxyphenyl)benzyl Alcohol

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
0 °C

Procedure

Ethyl 2-(3,4,5-trimethoxyphenyl)benzoate (655 mg) was dissolved in THF (20 mL), and to the solution lithium aluminum hydride (80 mg) was added at 0° C. under an argon atmosphere. The mixture was stirred at 0° C. for 1 hour as it is. A small amount of water and then sodium sulfate were added to the reaction mixture, and the reaction mixture was filtered through celite. The filtrate was concentrated under reduced pressure, and the resultant crude crystals were recrystallized from ethyl acetate-hexane to obtain the title compound.

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe resultant crude crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-ab6688c5a4c041a18cf40270231b93ac
Source dataset
uspto-grants-2003_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06509329B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes