1-Cyclopentylidenemethyl-2-methoxybenzene → 1-Cyclopentylmethyl-2-methoxybenzene

HRID 2210538Notes

Reaction equation

HRID 2210538 reaction equation
[C:1]1(=[CH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>CCO.[Pd]>[CH:1]1([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 193790781-Cyclopentylidenemethyl-2-methoxybenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 543564161-Cyclopentylmethyl-2-methoxybenzeneYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-cyclopentylidenemethyl-2-methoxybenzene (408 mmol, 76.7 g) and 10% Pd on carbon (7.67 g, 10% by weight) in absolute EtOH (767 mL) was shaken at room temperature under 54 psig of hydrogen pressure for 2.5 hours. Additional H2 was added to the vessel as necessary to maintain the initial pressure. The volatiles were removed in vacuo and the residue vacuum distilled to afford the title compound as a colorless oil (72.7 g, 94%). The desired fraction comes over at 85°-95° at 2.0-2.5 mm Hg and is used as such in the subsequent transformation.

Workup

  1. additionAdditional H2 was added to the vessel as necessary
  2. temperatureto maintain the initial pressure
  3. customThe volatiles were removed in vacuo
  4. distillationthe residue vacuum distilled

Sources & evidence

ORD record
ord-fc297475de334663b8e01a7670350351
Source dataset
uspto-grants-1995_10
Patent number
US05459151

Reaction notes

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