Acetic Anhydride → HCID 53634959, compound

HRID 1378561Notes

Reaction equation

HRID 1378561 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.[CH3:18][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>[CH3:18][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 69519o-Tolylacetic acidHCID 769854-(Methylthio)benzaldehyde

Product 1

HCID 53634959HCID 53634959, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of acetic anhydride (160 mL), 4-(methylthio)benzaldehyde (25.32 g, 166 mmol), 2-methylphenylacetic acid (24.95 g, 166 mmol), and triethylamine (17.89 g, 176 mmol) was heated to reflux for 2.67 hours. The reaction was cooled to 100° C., and water (200 mL) was added through an addition funnel. A clear oil formed that solidified upon chilling with an ice bath. The solid was collected by filtration, and recrystallized from a mixture of ethyl acetate and isooctane to give the desired acid in two crops (18.6 g, 39%): mp 134°-137° C. 1H NMR (CDCl3) 300 MHz 9.80 (br s, 1H), 7.91 (s,1H), 7.28 (m, 3H), 7.12 (d,J=7.5 Hz, 1H), 7.00 (d, J=8.5 Hz, 2H), 6.93 (d, J=8.5 Hz, 2H), 2.42 (s, 3H), 2.16 (s, 3H). High resolution mass spectrum Calc'd. for C17H16O2S: 284.0871. Found: 284.0863.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2.67 hours
  3. customA clear oil formed that solidified
  4. temperatureupon chilling with an ice bath
  5. filtrationThe solid was collected by filtration
  6. customrecrystallized from a mixture of ethyl acetate and isooctane

Sources & evidence

ORD record
ord-53fee3f36aa346b1a16896f53364a84c
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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