Acetic Anhydride → HCID 53753124, compound

HRID 1378567Notes

Reaction equation

HRID 1378567 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][CH:22]=[CH:21][C:20]=1[CH2:25][C:26]([OH:28])=[O:27].C(N(CC)CC)C>O>[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25](=[CH:14][C:13]1[CH:16]=[CH:17][C:10]([S:9][CH3:8])=[CH:11][CH:12]=1)[C:26]([OH:28])=[O:27]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 17124o-Chlorophenylacetic acidHCID 769854-(Methylthio)benzaldehyde

Product 1

HCID 53753124HCID 53753124, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of acetic anhydride (170 mL), 4-(methylthio)benzaldehyde (20.93 g, 137 mmol), 2-chlorophenylacetic acid (23.43 g, 137 mmol), and triethylamine (14.97 g, 147 mmol) was heated to reflux for 2 hours. The reaction was cooled to 90° C., and water (180 mL) was added through an addition funnel. A yellow solid that separated from the solution was isolated by filtration and air dried to afford the desired acid. The acid was recrystallized from a mixture of ethyl acetate and isooctane to afford 24.62 g (59%): mp 159°-164° C. 1H NMR (CDCl3) 300 MHz 7.97 (s, 1H), 7.48 (d, J=7.9 Hz, 1H), 7.17-7.35 (m, 3H), 7.02 (d, J=8.7 Hz 2H), 6.97 (d, J=8.7 Hz, 2H), 2.43 (s, 3H). High resolution mass spectrum Calc'd. for C16H13ClO2S: 304.0325. Found: 304.0334.

Workup

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

Sources & evidence

ORD record
ord-be4ce6d50e734bcbb501d8d8ea38e44e
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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