Acetyl chloride → Benzoic acid, 4-(ethoxyiminomethyl)-, methyl ester, hydrochloride (1:1)

HRID 514741Notes

Reaction equation

HRID 514741 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)#[N:2].[C:13]([Cl:16])(=[O:15])[CH3:14]>CCO>[ClH:16].[CH2:13]([O:15][C:1](=[NH:2])[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)[CH3:14]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 70791Methyl 4-cyanobenzoate2×

Product 1

HCID 90402661Benzoic acid, 4-(ethoxyiminomethyl)-, methyl ester, hydrochloride (1:1)Yield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A 2 L, three-necked round bottomed flask equipped with a magnetic stir bar, a temperature probe, addition funnel and nitrogen inlet was charged with methyl 4-cyanobenzoate (100 g, 620 mmol). The methyl 4-cyanobenzoate was dissolved in EtOH (438 mL) and cooled in an ice bath to 0° C. Acetyl chloride (353 mL, 4960 mmol) was added dropwise into the stirring solution over a 2 h period during which time an exotherm from 0° C. to 21° C. was noted. The reaction flask was capped, sealed with Parafilm®, and allowed to stir at 23° C. for 18 h. the resulting white solid was collected by vacuum filtration and washed with EtOH. The filtrate was concentrated until it became turbid and was then cooled in an ice bath. The resulting precipitate was collected by vacuum filtration, rinsed with EtOH, and the filtrate treated as described to give another crop. The solids were dried to give the title compound as a white solid (128 g, 85%): 1H NMR (400 MHz, CDCI3) δ 12.85 (br s, 1H), 12.20 (br s, 1H), 8.49 (m, 2H), 8.23 (m, 2H), 5.00 (q, 2H), 4.00 (s, 3H), 1.72 (t, 3H).

Workup

  1. customA 2 L, three-necked round bottomed flask equipped with a magnetic stir bar
  2. additiona temperature probe, addition funnel and nitrogen inlet
  3. customThe reaction flask was capped
  4. customsealed with Parafilm®
  5. filtrationwas collected by vacuum filtration
  6. washwashed with EtOH
  7. concentrationThe filtrate was concentrated until it
  8. temperaturewas then cooled in an ice bath
  9. filtrationThe resulting precipitate was collected by vacuum filtration
  10. washrinsed with EtOH
  11. additionthe filtrate treated
  12. customto give another crop
  13. customThe solids were dried

Sources & evidence

ORD record
ord-6abf2459512045d8ae4e55f323b8b377
Source dataset
uspto-grants-2015_08
Patent number
US09108932B2

Reaction notes

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