HCID 12743485, compound → HCID 12743495, compound

HRID 1369208Notes

Reaction equation

HRID 1369208 reaction equation
[C:1]([C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[CH2:17][C:18]([OH:20])=[O:19])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CC(O)=O.[Pd]>[CH2:1]([C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[CH2:17][C:18]([OH:20])=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 12743485HCID 12743485, compound

Product 1

HCID 12743495HCID 12743495, compoundYield 104.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

2-Benzoyl-4-methoxyphenylacetic acid (215.5 g, 0.80 mole) was divided into two equal portions, and each was dissolved in glacial AcOH (1.5 L) in a 2.5 L pressure bottle. 5% Pd/C (10 g, 0.0048 mole) was added to each, and each mixture was shaken at ambient temperature under hydrogen on a Parr apparatus. After 2.5 hr, the mixtures were filtered to remove the catalyst, and the filter pads were washed with EtOAc. The combined filtrates were concentrated to give the title compound (215 g, quantitative) as a heavy yellow oil which crystallized on standing: 1H NMR (250 MHz, CDCl3) δ7.05-7.35 (m, 6 H), 6.77 (dd, J=8.3, 2.7 Hz, 1 H), 6.71 (d, J=2.7 Hz, 1 H), 4.00 (s, 2 H), 3.76 (s, 3 H), 3.54 (s, 2 H).

Workup

  1. filtrationthe mixtures were filtered
  2. customto remove the catalyst
  3. washthe filter pads were washed with EtOAc
  4. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-1e1e977dd6fd435f9f2f666f05f9f0cf
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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