Diethyl Ether → HCID 178500766, compound

HRID 255668Notes

Reaction equation

HRID 255668 reaction equation
[C:1]1([CH:6]=[CH:7][C:8](=[O:14])[CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:5][CH2:4][CH2:3][CH:2]=1.[OH:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[C:18]([CH3:23])[CH:17]=1.[CH2:24](OCC)C>C1C=CC=CC=1>[C:1]1([CH:6]=[CH:7][C:8](=[O:14])[C:9](=[CH:24][NH:20][C:19]2[CH:21]=[CH:22][C:16]([OH:15])=[CH:17][C:18]=2[CH3:23])[C:10]([O:12][CH3:13])=[O:11])[CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 178194-Amino-m-cresolHCID 53916157HCID 53916157, compound

Product 1

HCID 178500766HCID 178500766, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 5 ml of benzene was dissolved 0.7 g of methyl 5-(cyclopenten-1-yl)-3-oxo-4-pentenoate, and 0.6 g of N,N-dimethylformamidodimethylacetal was added thereto. They were reacted at 70° C. for 1.5 hours. The reaction mixture was cooled to room temperature, and 0.44 g of 4-hydroxy-2-methylaniline was added thereto. The resulting mixture was subjected to reaction for addtional 1.5 hours. After completion of the reaction, 5 ml of diethyl ether was added, and the precipitated crystals were collected by filtration, and washed with 5 ml of diethyl ether to obtain 0.7 g of methyl 5-(cyclopenten-1-yl)-2-(4-hydroxy-2-methylphenylaminomethylene)-3-oxo-4-pentenoate having a melting point of 148°-151° C.

Workup

  1. additionwas added
  2. customThey were reacted at 70° C. for 1.5 hours
  3. customThe resulting mixture was subjected to reaction for addtional 1.5 hours
  4. additionwas added
  5. filtrationthe precipitated crystals were collected by filtration
  6. washwashed with 5 ml of diethyl ether

Sources & evidence

ORD record
ord-9184fe89b4ab4c5ea355be840e0a3868
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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