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

HRID 2116821Notes

Reaction equation

HRID 2116821 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 distillted 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

Sources & evidence

ORD record
ord-7623c73b31c1471bbf71e1d6c013a6fb
Source dataset
uspto-grants-2008_10
Patent number
US07439379B2

Reaction notes

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