HCID 57712919, compound → 5-(2,4-dimethoxyphenyl)pentanoic acid

HRID 1983428Notes

Reaction equation

HRID 1983428 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1/[CH:11]=[CH:12]/[CH2:13][CH2:14][C:15]([OH:17])=[O:16]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16]

Participants

3

Reactant 1

HCID 57712919HCID 57712919, compound

Product 1

HCID 74719765-(2,4-dimethoxyphenyl)pentanoic acidYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 1-L hydrogenation flask was charged with 36.2 g of 5-(2,4-dimethoxyphenyl)-4-pentenoic acid (3a) and 400 ml of glacial acetic acid. The flask was flushed with argon and 2 g of (10% Pd/C) were added to the flask, which was then attached to the hydrogenator. The hydrogenation bottle was evacuated, and charged with hydrogen to 40 to 50 psi. The reaction was run overnight until no further hydrogen was being consumed. The solution was filtered through Cellite (diatomaceous earth). The solvent was evaporated, and the residue dried in vacuo. The yield was 99%. 1H NMR (DMSO-d6) δ: 12.01 (br s, 1H), 6.99 (d, J=8.2 Hz, 1H), 6.49 (d, J=2 Hz, 1H), 6.41 (dd, J1=2 Hz, J2=8.2 Hz, 1H), 3.74 (s, 3H), 3.72 (s, 3H), 2.45 (t, 2H), 2.20 (t, 2H), 1.47 (m, 4H).

Workup

  1. customThe flask was flushed with argon and 2 g of (10% Pd/C)
  2. additionwere added to the flask, which
  3. customThe hydrogenation bottle was evacuated
  4. additioncharged with hydrogen to 40 to 50 psi
  5. customwas being consumed
  6. filtrationThe solution was filtered through Cellite (diatomaceous earth)
  7. customThe solvent was evaporated
  8. customthe residue dried in vacuo

Sources & evidence

ORD record
ord-f40e430b32904c9da24c15ad3301a74d
Source dataset
uspto-grants-2009_06
Patent number
US07541454B2

Reaction notes

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