Formic Acid → 2-Methyl-2-(3-nitrophenyl)propanoic acid

HRID 863206Notes

Reaction equation

HRID 863206 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].C(N(CC)CC)C.C(O)=O>C(#N)C.[Pd]>[N+:14]([C:3]1[CH:4]=[C:5]([C:8]([CH3:13])([CH3:12])[C:9]([OH:11])=[O:10])[CH:6]=[CH:7][CH:2]=1)([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 227094342-(4-Chloro-3-nitrophenyl)-2-methylpropanoic acid

Product 1

HCID 186218202-Methyl-2-(3-nitrophenyl)propanoic acidYield 92.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6342AcetonitrileSolvent

Procedure

The procedure is similar to that described in Example 1, but starting with 6.3 g of 2-(4-chloro-3-nitrophenyl) -2-methylpropionic acid, 7.62 ml of triethylamine, 0.6 g of 5% palladium-on-charcoal and 1.46 ml of formic acid in 100 ml of acetonitrile. 5.0 g of 2-(3-nitrophenyl)-2-methylpropionic acid are thus obtained in the form of an orange oil [NMR spectrum (DMSO-d6, 200 MHz): 1.57 (s, 6H); 7.65 (t, J=7 Hz, 1H); 7.9 (d, J=7 Hz, 1H); 8.13 (d, J=7 Hz, 1H); 8.15 (s, 1H); 12.5 (broad s, acidic OH)].

Sources & evidence

ORD record
ord-0e64ccf831d14914bad1588c2e099a42
Source dataset
uspto-grants-1998_02
Patent number
US05719317

Reaction notes

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