Acetyl chloride → HCID 90402711, compound

HRID 514742Notes

Reaction equation

HRID 514742 reaction equation
[C:1]([Cl:4])(=[O:3])[CH3:2].[C:5]([C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1)#[N:6]>CCO>[ClH:4].[CH2:1]([O:3][C:5](=[NH:6])[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 120874-Cyanobenzoic acid

Product 1

HCID 90402711HCID 90402711, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

A 500 mL, three-necked flask, equipped with a magnetic stir bar, nitrogen inlet, addition funnel, and a temperature probe was charged with anhydrous EtOH (125 mL). The vessel was cooled to 5° C. and acetyl chloride (97 mL, 1332 mmol) was added at a rate that maintained the temperature range of 5 to 10° C. When the addition was complete, 4-cyanobenzoic acid (25 g, 167 mmol) was added in portions over 15 min. No exotherm was noted during the addition of the solid. When the addition was complete, the white suspension was allowed to warm to 25° C. The reaction vessel was sealed with Parafilm® and stirred at 23° C. for 18 h. The Write suspension was vacuum filtered and the solid was rinsed with EtOH and dried to constant mass, furnishing 4-(ethoxy(imino)methyl)benzoic acid hydrochloride as a white solid (25 g, 65%): 1H NMR (400 MHz, DMSO-d6) δ 12.44 (br s, 1H), 8.26 (m, 2H), 8.14 (m, 2H), 4.70 (q, 2H), 1.51 (t, 3H). The filtrate was concentrated and treated with ether to give a white solid. The solid was collected by vacuum filtration and rinsed with ether to give ethyl 4-(ethoxy(imino)methyl)benzoate hydrochloride as a white solid (11 g, 25%): 1H NMR (400 MHz, DMSO-d6) δ 12.07 (br s, 1H), 8.24 (m, 2H), 8.15 (m, 2H), 4.66 (q, 3H), 4.37 (q, 3H), 1.49 (t, 3H), 1.35 (q, 3H).

Workup

  1. customA 500 mL, three-necked flask, equipped with a magnetic stir bar, nitrogen inlet, addition funnel
  2. temperaturemaintained the temperature range of 5 to 10° C
  3. additionWhen the addition
  4. additionNo exotherm was noted during the addition of the solid
  5. additionWhen the addition
  6. temperatureto warm to 25° C
  7. customThe reaction vessel was sealed with Parafilm®
  8. filtrationfiltered
  9. washthe solid was rinsed with EtOH
  10. customdried to constant mass

Sources & evidence

ORD record
ord-dc6b399ac697432282a79cff434c0d1a
Source dataset
uspto-grants-2015_08
Patent number
US09108932B2

Reaction notes

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