4-((1E,3E)-4-Methoxycarbonyl-buta-1,3-dienyl) 3-methyl-benzoic acid tert-butyl ester → 4-(4-Methoxycarbonyl-butyl)-3-methyl-benzoic Acid Tert-butyl Ester

HRID 220826Notes

Reaction equation

HRID 220826 reaction equation
[C:1]([O:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[CH:15]=[CH:16]/[C:17]([O:19][CH3:20])=[O:18])=[C:9]([CH3:21])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[C:9]([CH3:21])[CH:8]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 866266384-((1E,3E)-4-Methoxycarbonyl-buta-1,3-dienyl) 3-methyl-benzoic acid tert-butyl ester

Product 1

HCID 575553334-(4-Methoxycarbonyl-butyl)-3-methyl-benzoic Acid Tert-butyl EsterYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-((1E,3E)-4-Methoxycarbonyl-buta-1,3-dienyl) 3-methyl-benzoic acid tert-butyl ester from Example E31.2 (1.54 g, 5.1 mmol) was dissolved in methanol (40 ml) and hydrogenated over 10% Pd/C catalyst (200 mg) for 5 h. The mixture was filtered through Celite® filter agent and the filtrate was concentrated in vacuo to yield the title compound (1.43 g, 92%).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. filtrationfilter agent
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b1639eb2e61d40ddb7f8c3b7af4c2150
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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