Hydrochloric Acid → 2-Ethoxy-3-(4-nitrophenyl)prop-2-enoic acid

HRID 526033Notes

Reaction equation

HRID 526033 reaction equation
[CH2:1]([O:3][C:4](=[CH:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)[C:5]([O:7]CC)=[O:6])[CH3:2].CN(C=O)C.[OH-].[Na+].Cl>O>[CH2:1]([O:3][C:4](=[CH:10][C:11]1[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=1)[C:5]([OH:7])=[O:6])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 66905768Ethyl 2-ethoxy-3-(4-nitrophenyl)prop-2-enoate

Product 1

HCID 669056312-Ethoxy-3-(4-nitrophenyl)prop-2-enoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 2-ethoxy-3-(4-nitrophenyl)acrylate containing 3.6 wt % DMF (26.07 g corrected, 98.3 mmol) was dissolved in IMS (500 ml) and a solution of NaOH (1.44 g, 36.1 mmol) in water (260 ml) was added. The resulting mixture was stirred at ambient temperature for 18 hr then acidified with 1M HCl (120 ml) and the resulting solid collected by filtration, washed with water (2×100 ml) and suction dried on the filter for 30 mins, followed by vacuum oven drying at 18° C. for 18 hr. 2-Ethoxy-3-(4-nitrophenyl)acrylic acid was thus obtained as an orange solid containing water of crystallisation (18.4 g, 79%).

Workup

  1. filtrationthe resulting solid collected by filtration
  2. washwashed with water (2×100 ml) and suction
  3. customdried on the
  4. filtrationfilter for 30 mins
  5. customdrying at 18° C. for 18 hr

Sources & evidence

ORD record
ord-d4126667f56a401fab5602b743c61a8a
Source dataset
uspto-grants-2016_05
Patent number
US09345680B2

Reaction notes

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