Acetic Anhydride → 4'-Acetoxy-biphenyl-4-carboxylic acid
Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:17](OC(=O)C)(=[O:19])[CH3:18]>S(=O)(=O)(O)O.O>[C:17]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)(=[O:19])[CH3:18]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
50 Grams (234 mmol) of 4′-hydroxybiphenyl-4-carboxylic acid and 238 g (2.34 mol) of acetic anhydride were placed in a reactor, and while these stirred, 0.1 g of concentrated sulfuric acid was added. The mixture was stirred until heat generation ceased, and the mixture was further heated at 80° C. for 4 hours with stirring and then gradually cooled to room temperature. While the reaction mixture was cooled in an ice bath, 500 g of water was gradually added, and the mixture was stirred at room temperature for 3 hours to quench unreacted acetic anhydride. A precipitated white solid was recovered by filtration, washed with water to remove acetic acid, and dried with a vacuum drier to give 59.8 g of an end compound (yield 99%).
Workup
- temperatureuntil heat generation
- stirringwith stirring
- temperaturegradually cooled to room temperature
- temperatureWhile the reaction mixture was cooled in an ice bath
- stirringthe mixture was stirred at room temperature for 3 hours
- customto quench unreacted acetic anhydride
- filtrationA precipitated white solid was recovered by filtration
- washwashed with water
- customto remove acetic acid
- customdried with a vacuum drier
Sources & evidence
- ORD record
- ord-2098efd5624e424d87d11ed2c2150458
- Source dataset
- uspto-grants-2004_05
- Patent number
- US06730371B2
Reaction notes
Loading…