3-(Prop-1-ynyl)-4-propylbenzoic acid → 3,4-Dipropylbenzoic acid

HRID 710409Notes

Reaction equation

HRID 710409 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[CH2:13][CH2:14][CH3:15])[C:7]([OH:9])=[O:8])#[C:2][CH3:3]>CCO.[Pd]>[CH2:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[CH2:13][CH2:14][CH3:15])[C:7]([OH:9])=[O:8])[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 667267763-(Prop-1-ynyl)-4-propylbenzoic acid

Product 1

HCID 667268843,4-Dipropylbenzoic acidYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the product of Step B (0.19 g; 0.94 mmol) and 10% Pd/C (0.1 g) in EtOH (15 ml) was stirred over the weekend under H2 (10 psi; Parr apparatus). The catalyst was removed by filtration through Celite pad, washed with CH2Cl2 (2×20 ml) and combined filtrates were evaporated to dryness to give the title compound (0.17 g; 88%) as creamy solid. 1H-NMR (CDCl3) 0.93-1.0 (m, 6H); 1.55-1.69 (m, 4H); 2.6-2.66 (m, 4H); 6.6 (broad s, 1H); 7.2-7.27 (m, 1H+CDCl3); 7.83-7.88 (m, 2H).

Workup

  1. customThe catalyst was removed by filtration through Celite pad
  2. washwashed with CH2Cl2 (2×20 ml)
  3. customwere evaporated to dryness

Sources & evidence

ORD record
ord-aa693e134f3b422f9e68b9039126eb71
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

Loading…