Acetic Acid → 3,5-Dimethyl-4-(3'-iso-propyl-4'-methoxyphenoxy)phenylacetic acid
Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4](CC#N)[CH:5]=[C:6]([CH3:20])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH:17]([CH3:19])[CH3:18])[CH:10]=1.OS(O)(=O)=O.[C:29]([OH:32])(=[O:31])[CH3:30]>>[CH3:20][C:6]1[CH:5]=[C:4]([CH2:30][C:29]([OH:32])=[O:31])[CH:3]=[C:2]([CH3:1])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH:17]([CH3:18])[CH3:19])[CH:10]=1Participants
Conditions
- Temperature
- 105 °C
Procedure
To a stirred solution of 3,5-dimethyl-4-(3′-iso-propyl-4′-methoxyphenoxy)phenylacetonitrile (0.75 g, 2.42 mmol) in acetic acid (7 mL) was added a 50% solution of H2SO4 (14 mL). The reaction mixture was heated at 105° C., for 3 h, cooled to room temperature and poured into ice water (100 mL). The mixture was stirred for 1 h and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford 3,5-dimethyl-4-(3′-iso-propyl-4′-methoxyphenoxy)phenylacetic acid as a brownish solid (0.62 g, 85%, m.p.: 118-120° C.): 1H NMR (300 MHz, CDCl3): δ 7.11 (s, 2 H), 6.82 (d, J=2.7 Hz, 1 H), 6.80 (d, J=8.7 Hz, 1 H), 6.37 (dd, J=3.3, 8.7 Hz, 1 H), 3.80 (s, 3 H), 3.61 (s, 2 H), 3.38-3.25 (m, 1 H), 2.11 (s, 6 H), 1.17 (d, J=7.2 Hz, 6 H); TLC conditions: Uniplate silica gel, 250 microns; mobile phase=ethyl acetate-hexanes (1:1); Rf=0.2.
Workup
- temperaturecooled to room temperature
- extractionextracted with ethyl acetate (3×50 mL)
- washThe combined organic layers were washed with water and brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-56f8a045cef746b09c264a07e894ce1d
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07514419B2
Reaction notes
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