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

HRID 526028Notes

Reaction equation

HRID 526028 reaction equation
[CH3:1][O:2][C:3](=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)[C:4]([O:6]C)=[O:5].[OH-].[Na+].Cl>O>[CH3:1][O:2][C:3](=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66905801HCID 66905801, compound

Product 1

HCID 669056512-Methoxy-3-(4-nitrophenyl)prop-2-enoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
18 °C

Procedure

Methyl 2-methoxy-3-(4-nitrophenyl)acrylate (7.8 g, 32.8 mmol) was dissolved in IMS (156 ml). A solution of NaOH (1.44 g, 36.1 mmol) in water (78 ml) was added and the mixture stirred at ambient temperature (18° C.) for 18 hr. The reaction mixture was acidified with 1M HCl (120 ml) and the resulting precipitated solid was collected by filtration, washed with water (2×100 ml) and partially suction dried on the filter for 30 mins, followed by vacuum oven drying at 18° C. for 18 hr. Thus 2-methoxy-3-(4-nitrophenyl)acrylic acid was afforded as a tan solid containing some water of crystallisation (6.7 g, 91%).

Workup

  1. customthe resulting precipitated solid
  2. filtrationwas collected by filtration
  3. washwashed with water (2×100 ml)
  4. custompartially suction dried on the
  5. filtrationfilter for 30 mins
  6. customdrying at 18° C. for 18 hr

Sources & evidence

ORD record
ord-882aa7e70dbf45179e84520f7449d946
Source dataset
uspto-grants-2016_05
Patent number
US09345680B2

Reaction notes

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