Sodium borohydride → 4-(3-Phenylpropoxy)benzenemethanol

HRID 1739400Notes

Reaction equation

HRID 1739400 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>C(O)C.C(OCC)(=O)C.Cl>[C:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([CH2:15][OH:16])=[CH:17][CH:18]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 211912554-(3-Phenylpropoxy)benzaldehyde

Product 1

HCID 285616024-(3-Phenylpropoxy)benzenemethanolYield 83%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

4.9 g of 4-(3-phenylpropyloxy)benzaldehyde were dissolved in 30 ml of ethanol, and 0.39 g of sodium borohydride were added to the resultant solution, then the solution was stirred for 1 hour at room temperature. After completed the reaction, the solvent used was distillated under reduced pressure, and the residue obtained was dissolved in a mixture of ethyl acetate and dilute hydrochloric acid. After washing the ethyl acetate layer with dilute hydrochloric acid, dilute alkaline aqueous solution and water in series, the organic layer was then dried with anhydrous magnesium sulfate, and the solvent used was distillated under reduced pressure, thereby affording 4.1 g of 4-(3-phenylpropyloxy)benzyl alcohol.

Workup

  1. customthe reaction
  2. customthe residue obtained
  3. washAfter washing the ethyl acetate layer with dilute hydrochloric acid
  4. additiondilute alkaline aqueous solution and water in series
  5. dry with materialthe organic layer was then dried with anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-1566275acdab43ef87b3284a9c71a260
Source dataset
uspto-grants-1999_10
Patent number
US05965743

Reaction notes

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