HCID 22720364, compound → 2-Methoxy-6-nitrophenylacetic acid

HRID 1582437Notes

Reaction equation

HRID 1582437 reaction equation
CC(C)=[O:3].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:8]=1[CH2:16][CH2:17][OH:18].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>>[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:8]=1[CH2:16][C:17]([OH:3])=[O:18]

Participants

3

Reactant 2

HCID 22720364HCID 22720364, compoundHCID 131709961Jones' reagent

Product 1

HCID 5643152-Methoxy-6-nitrophenylacetic acidYield 98.4%

Conditions

Temperature
0 °C

Procedure

A solution of 4.3 g of 2-(2-methoxy-6-nitrophenyl)-1-ethanol acetone (117 mL) is slowly treated with a solution of Jones Reagent (31 mL). The volatiles are removed under reduced pressure, diluted with 5M sodium hydroxide, cooled to 0° C., and treated slowly with concentrated H2SO4. This solution is extracted four times with ethyl acetate with the combine organics washed with brine, dried over NaSO4, filtered, and concentrated. The crude material is purified by LC (10% MeOH/CH2Cl2) to give 3.5 g of 2-(2-methoxy-6-nitrophenyl)acetic acid as a yellow/gold solid. 1H NMR (300 MHz, DMSO-d6) δ3.84 (s, 3H), 3.87 (s, 2H), 7.42 (d, J=7 Hz, 1H), 7.52 (t, J=8 Hz, 1H), 7.59 (dd, J=1, 8 Hz, 1H); 13C NMR (75 MHz, CDCl3) δ157.9, 150.7, 127.5, 120.1, 115.3, 114.8, 56.4, 11.1; IR (drift) 3020, 2983, 2945, 2888, 2840, 1710, 1531, 1471, 1434, 1353, 1274, 1256, 1229, 1058, 799 cm−1. HRMS (FAB) calculated for C9H9NO5+H1 212.0559, found 212.0555.

Workup

  1. customThe volatiles are removed under reduced pressure
  2. additiondiluted with 5M sodium hydroxide
  3. additiontreated slowly with concentrated H2SO4
  4. extractionThis solution is extracted four times with ethyl acetate with the combine
  5. washorganics washed with brine
  6. dry with materialdried over NaSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material is purified by LC (10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-3e474090a70c4dc78986281a98937f13
Source dataset
uspto-grants-2004_05
Patent number
US06734301B2

Reaction notes

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