Acetic Anhydride → HCID 54305885, compound

HRID 1378565Notes

Reaction equation

HRID 1378565 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.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[CH2:23][C:24]([OH:26])=[O:25].C(N(CC)CC)C>O>[CH3:8][S:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[C:23]([C:19]2[S:18][CH:22]=[CH:21][CH:20]=2)[C:24]([OH:26])=[O:25])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 159702-Thiopheneacetic acidHCID 769854-(Methylthio)benzaldehyde

Product 1

HCID 54305885HCID 54305885, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of acetic anhydride (90 mL), 4-(methylthio)benzaldehyde (13.17 g, 82.2 mmol), 2-(2-thienyl)acetic acid (12.09 g, 83.3 mmol), and triethylamine (8.60 g, 85 mmol) was heated to reflux for 4 hours. The reaction was cooled to 85° C., and water (80 mL) was added through an addition funnel. A brown solid was isolated by filtration and air dried to afford the propenoic acid (8.48 g, 37%): mp 201°-206° C. 1H NMR (DMSO-d6) 300 MHz 12.80 (br s, 1H), 7.77 (s,1H), 7.60 (d, J=5.2 Hz, 1H), 7.09 (m, 5H), 6.92 (d, J=3.3 Hz, 1H), 2.42 (s, 3H). 13C NMR (DMSO-d6) 168.24, 141.60, 141.30, 136.84, 131.08, 130.86, 128.46, 127.86, 125.51, 125.28, 14.52. Mass spectrum: M+H=277.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hours
  3. customA brown solid was isolated by filtration and air
  4. customdried

Sources & evidence

ORD record
ord-5fe76bf6eb4246dd8764934d6ee59319
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

Loading…