Acetic Acid → HCID 69426186, compound

HRID 1269581Notes

Reaction equation

HRID 1269581 reaction equation
S(=O)(=O)(O)O.C(O[C:13](CC)([CH2:38]C)[C:14]1[CH:19]=[C:18]([CH:20]([CH3:22])[CH3:21])[C:17]([O:23][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[C:26]([O:33][CH3:34])[CH:25]=2)=[C:16]([CH:35]([CH3:37])[CH3:36])[CH:15]=1)(=O)CC([O-])=O.[C:42]([OH:45])(=[O:44])C>O>[CH:20]([C:18]1[CH:19]=[C:14]([CH:13]([CH3:38])[C:42]([OH:45])=[O:44])[CH:15]=[C:16]([CH:35]([CH3:36])[CH3:37])[C:17]=1[O:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[C:26]([O:33][CH3:34])[CH:25]=1)([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 86592348HCID 86592348, compound

Product 1

HCID 69426186HCID 69426186, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Sulphuric acid (1.0 mL, 20%) was added to a mixture of diethyl(3,5-diisopropyl-4-[3-methoxy-4-nitrophenoxy]benzyl) malonate (1.4 g), acetic acid (5 mL) and water (5 mL). After heating for 8 hours at 80° C., the reaction mixture was concentrated and ethyl acetate was added to the residue. The organic phase was washed with water and brine. After recrystallization (ethyl acetate/petrolium ether), 1.1 g of 3,5-diisopropyl-4-(3-methoxy-4-nitrophenoxy)phenylpropionic acid was obtained.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionethyl acetate was added to the residue
  3. washThe organic phase was washed with water and brine
  4. customAfter recrystallization (ethyl acetate/petrolium ether)

Sources & evidence

ORD record
ord-62a1ee5aefe1445b8f5087a350e0b117
Source dataset
uspto-grants-2007_04
Patent number
US07199265B2

Reaction notes

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