HCID 66743536, compound → 4-(2,3-Dimethoxyphenyl)butanoic acid

HRID 2199533Notes

Reaction equation

HRID 2199533 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH:11]=[CH:12][CH2:13][C:14]([OH:16])=[O:15]>CCO.[Pd]>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15]

Participants

4

Reactant 1

HCID 66743536HCID 66743536, compound

Product 1

HCID 2991614-(2,3-Dimethoxyphenyl)butanoic acidYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Acid 5 (3.7 g, 0.017 mol) was dissolved in 25 mL absolute EtOH and added to a Parr hydrogenation bottle containing 0.6 g of 10% Pd/C. The bottle was then pressurized to 25 psi H2 and shaken for 2 h. The contents were then filtered through Celite, the solvents were evaporated, and the resulting oil dried under high vacuum to yield a grey solid (3.7 g, 0.017 mol, quant. yield). The solid was recrystallized from EtOAc/hexanes to produce fine white needles; mp 58-59° C. (lit.27 mp 58.5-60° C.). 1H NMR: (300 MHz, CDCl3): δ 6.97 (t, 1H, J=8 Hz, ArH); 6.76 (d, 1H, J=8 Hz, ArH); 6.75 (d, 1H, J=8 Hz, ArH); 3.84 (s, 3H, ArOCH3); 3.80 (s, 3H, ArOCH3); 2.67 (t, 2H, J=7 Hz, HO2CCH2CH2); 2.37 (t, 2H, J=7 Hz, ArCH2); 1.92 (p, 2H, J=7 Hz, HO2CCH2CH2). ESIMS (M+Na+)=247.

Workup

  1. additionadded to a Parr hydrogenation bottle
  2. filtrationThe contents were then filtered through Celite
  3. customthe solvents were evaporated
  4. customthe resulting oil dried under high vacuum

Sources & evidence

ORD record
ord-5657af08c9dd4cb68d5b8b1b4b466c66
Source dataset
uspto-grants-2016_06
Patent number
US09359303B2

Reaction notes

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