Acetic Anhydride → HCID 54006809, compound

HRID 1378569Notes

Reaction equation

HRID 1378569 reaction equation
C(OC(=O)C)(=O)C.[CH3:8][S:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]([OH:28])=[O:27])=[CH:21][CH:20]=1.C(N(CC)CC)C>O>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([C:25](=[CH:14][C:13]2[CH:16]=[CH:17][C:10]([S:9][CH3:8])=[CH:11][CH:12]=2)[C:26]([OH:28])=[O:27])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 15880(4-Chlorophenyl)acetic acidHCID 769854-(Methylthio)benzaldehyde

Product 1

HCID 54006809HCID 54006809, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of acetic anhydride (80 mL), 4-(methylthio)benzaldehyde (9.81 g, 61.2 mmol), 4-chlorophenylacetic acid (12.03 g, 70.5 mmol), and triethylamine (7.49 g, 7.42 mmol) was heated to reflux for 7 hours. The reaction was cooled to 90° C., and water (100 mL) was added through an addition funnel. A yellow solid separated from the solution which was isolated by filtration and air dried to afford the desired acid. The acid was recrystallized from toluene (9.59 g, 51%): mp 185°-187° C. 1H NMR (CDCl3) 300 MHz 7.91 (s, 1H), 7.35 (d, J=8.3 Hz, 1H), 7.17-7.35 (m, 3H), 7.03 (d, 2H), 7.00 (d, J=8.7 Hz, 2H), 2.44 and 2.36 (s, 3H). Mass spectrum: M+H=305.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 7 hours
  3. customA yellow solid separated from the solution which
  4. customwas isolated by filtration and air
  5. customdried

Sources & evidence

ORD record
ord-957e1863247348edb0ec7a279fcf9c0c
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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