Triethylamine → HCID 57421382, compound

HRID 553017Notes

Reaction equation

HRID 553017 reaction equation
[CH3:1][O:2][C:3]([C:5]([CH3:19])([CH3:18])[CH2:6][CH:7]=[CH:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)=[O:4].C(N(CC)CC)C>C(O)C.[Pd].C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]([CH3:19])([CH3:18])[CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:16][CH:17]=1)=[O:4]

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 67164573HCID 67164573, compound

Product 1

HCID 57421382HCID 57421382, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(4-Methoxycarbonyl-4-methyl-pent-1-enyl)-benzoic acid (900 mg, 3.4 mmol, 1 eq.) was dissolved in ethanol (13 ml) and triethylamine (568 μl, 4.1 mmol, 1.2 eq.) and palladium on carbon (90 mg, 10% Pd/C) were then added. The mixture was stirred under hydrogen atmosphere for 20 h. Reaction mixture was filtered over celite and washed with ethanol. The filtrate was evaporated to yield a yellow oil. This oil was dissolved in ethyl acetate and washed with a 1N aqueous hydrochloric acid solution. The aqueous layer was removed and the organic layer was washed with water, and brine, then dried over magnesium sulfate, filtered and concentrated to give 4-(4-methoxycarbonyl-4-methyl-pentyl)-benzoic acid (763 mg, 85%).

Workup

  1. customReaction mixture
  2. filtrationwas filtered over celite
  3. washwashed with ethanol
  4. customThe filtrate was evaporated
  5. customto yield a yellow oil
  6. washwashed with a 1N aqueous hydrochloric acid solution
  7. customThe aqueous layer was removed
  8. washthe organic layer was washed with water, and brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-7b2b03c55b9a44fe89949d1e221b1162
Source dataset
uspto-grants-2011_05
Patent number
US07951950B2

Reaction notes

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