Water → 2-(2,3,4,5-Tetramethylcyclopentadienyl)benzylalcohol

HRID 15697Notes

Reaction equation

HRID 15697 reaction equation
[CH3:1][C:2]1[CH:3]([C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH:12]=[O:13])[C:4]([CH3:9])=[C:5]([CH3:8])[C:6]=1[CH3:7].[BH4-].[Na+].C1(C)C=CC=CC=1.O>C(O)C>[CH3:1][C:2]1[CH:3]([C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH2:12][OH:13])[C:4]([CH3:9])=[C:5]([CH3:8])[C:6]=1[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 4311764Sodium borohydrideHCID 1317271152-(2,3,4,5-Tetramethylcyclopentadienyl)benzaldehyde

Product 1

HCID 1317271142-(2,3,4,5-Tetramethylcyclopentadienyl)benzylalcoholYield 97.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(2,3,4,5-tetramethylcyclopentadienyl)benzaldehyde (2.26 g, 10.0 mmol) in ethanol (29.0 mL) was added sodium borohydride (0.42 g, 11.0 mmol) at room temperature and the mixture was stirred for 3 hrs. To the reaction mixture solution were added toluene (20.0 mL) and deionized water (20.0 mL) to separate an organic layer and an aqueous layer. The organic layer was dried over sodium sulfate and the solvent was then distilled off to give 2-(2,3,4,5-tetramethylcyclopentadienyl)benzylalcohol (2.23 g, yield 96.0%) as a pale oily substance.

Workup

  1. customto separate an organic layer
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. distillationthe solvent was then distilled off

Sources & evidence

ORD record
ord-df53085eba674a4bbafddd9a33b8b7e5
Source dataset
uspto-grants-2010_06
Patent number
US07732643B2

Reaction notes

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