Water → {2-(2,3,4,5-Tetramethylcyclopentadienyl)phenyl}phenylmethylalcohol

HRID 2242570Notes

Reaction equation

HRID 2242570 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].[C:18]1([Li])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O.C1(C)C=CC=CC=1>O1CCCC1.C1CCCCC1.CCOCC>[CH3:1][C:2]1[CH:3]([C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH:12]([OH:13])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:4]([CH3:9])=[C:5]([CH3:8])[C:6]=1[CH3:7]

Participants

8

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 1317271152-(2,3,4,5-Tetramethylcyclopentadienyl)benzaldehydeHCID 178506676HCID 178506676, compound

Product 1

HCID 131727116{2-(2,3,4,5-Tetramethylcyclopentadienyl)phenyl}phenylmethylalcoholYield 87%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolvent

Procedure

To a solution of 2-(2,3,4,5-tetramethylcyclopentadienyl)benzaldehyde (2.0 g, 8.80 mmol) in tetrahydrofuran (34.0 mL) was added dropwise a 1.05 M solution of phenyllithium in cyclohexane and ether (17.7 mL) at −78° C. The temperature of the mixture was raised to room temperature and the mixture was stirred for 4 hrs. To the reaction mixture solution were added deionized water (20.0 mL) and toluene (20.0 mL) to separate an organic layer and an aqueous layer. The organic layer was dried over sodium sulfate, then distilled to remove the solvent, and purified by a silica gel column (hexane/ethyl acetate=9/1) to give {2-(2,3,4,5-tetramethylcyclopentadienyl)phenyl}phenylmethylalcohol (2.83 g, yield 87.0%) as a pale yellow oily substance. 1H-NMR (CDCl3): δ 7.77-6.91 (4H), 6.45-5.55 (2H), 3.21-2.25 (1H), 1.88-1.45 (9H), 1.16-0.82 (3H);

Workup

  1. customto separate an organic layer
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. distillationdistilled
  4. customto remove the solvent
  5. custompurified by a silica gel column (hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-327496f4995d4b6fa312908b6cab0b8b
Source dataset
uspto-grants-2010_03
Patent number
US07671226B2

Reaction notes

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