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Water → 2-(2-Chloro-4-nitrophenyl)acetic acid

HRID 1517249
Notes
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Reaction equation

HRID 1517249 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH:11](C(OC)=O)[C:12]([O:14]C)=[O:13].S(=O)(=O)(O)O.O>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][C:12]([OH:14])=[O:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric Acid2×HCID 11414995Dimethyl 2-(2-chloro-4-nitrophenyl)malonate

Product 1

HCID 125105882-(2-Chloro-4-nitrophenyl)acetic acidYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

Dimethyl 2-(2-chloro-4-nitrophenyl)malonate (96 mmol) was suspended in acetic acid (175 mL). Conc. sulfuric acid (3.5 mL) was added and the mixture was stirred at 80° C. over night. Water (30 mL) was added and the mixture was stirred at 100° C. for 2 h. after which conc. sulfuric acid (1 mL) was added. The mixture was stirred at room temperature over night. The formed precipitate was filtered off and washed with water. The remaining solid was dried under reduced pressure to give 2-(2-chloro-4-nitrophenyl)acetic acid as a solid (80%).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at room temperature over night
  3. filtrationThe formed precipitate was filtered off
  4. washwashed with water
  5. customThe remaining solid was dried under reduced pressure

Sources & evidence

ORD record
ord-ef6da61c70e44ad6b42210fe8b0c91e7
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08232283B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes