4-(1-Cyclohexen-1-yl)-3-ethylbenzoic acid → 4-Cyclohexyl-3-ethylbenzoic acid

HRID 423309Notes

Reaction equation

HRID 423309 reaction equation
[C:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=2[CH2:16][CH3:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1>CO.[Pd]>[CH:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=2[CH2:16][CH3:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 593168044-(1-Cyclohexen-1-yl)-3-ethylbenzoic acid

Product 1

HCID 593168004-Cyclohexyl-3-ethylbenzoic acidYield 97.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-(1-cyclohexen-1-yl)-3-ethylbenzoic acid (D18) (803 mg, 3.49 mmol) was dissolved in methanol (70 mL) and hydrogenated on an H-Cube using a palladium on carbon cartridge. The product solution was concentrated in vacuo to give the title compound as a white solid (792 mg, 3.41 mmol). δH (methanol-d4, 400 MHz): 7.82-7.68 (2H, m), 7.33 (1H, d), 2.83 (1H, m), 2.73 (2H, q), 1.87 (2H, m), 1.85-1.70 (3H, m), 1.58-1.30 (5H, m), 1.22 (3H, t). LCMS (ES): no mass ion observed.

Workup

  1. concentrationThe product solution was concentrated in vacuo

Sources & evidence

ORD record
ord-aebbfadfca7346f58c8dfd542e821c13
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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