Sodium Methoxide → HCID 54711092, compound

HRID 437364Notes

Reaction equation

HRID 437364 reaction equation
[CH2:1]([N:3]([C:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=1[C:13]([OH:15])=O)[C:4](=[O:6])[CH3:5])[CH3:2].C[O-].[Na+]>O1CCOCC1>[CH2:1]([N:3]1[C:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[C:13]([OH:15])=[CH:5][C:4]1=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 54006689HCID 54006689, compound

Product 1

HCID 54711092HCID 54711092, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of the ethyl and methyl esters (60:40 ratio) of 2-(N-ethyl-acetamido) cyclohex-1-ene-1-carboxylic acid (10 g; 0.043 mole) in dry dioxan (100 ml) was treated with sodium methoxide (2.54 g; 0.047 mole) and the mixture heated for 2 hrs. at 100° C. A white solid separated within a few minutes. After cooling the precipitate was filtered free of dioxan, taken up in a minimum of water and brought to pH 4 with concentrated hydrochloric acid. The product separated as a white solid which after filtration was recrystallised from glacial acetic acid, m.p. 355° -358° C (d).

Workup

  1. temperaturethe mixture heated for 2 hrs
  2. customat 100° C
  3. customA white solid separated within a few minutes
  4. temperatureAfter cooling the precipitate
  5. filtrationwas filtered free of dioxan
  6. customThe product separated as a white solid which
  7. filtrationafter filtration
  8. customwas recrystallised from glacial acetic acid, m.p. 355° -358° C (d)

Sources & evidence

ORD record
ord-37ad2fbf2b1849d19294fa6b236406f9
Source dataset
uspto-grants-1977_06
Patent number
US04031099

Reaction notes

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