Hydrochloric Acid → 4-Acetyl-2-methylbenzoic acid
Reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]([O:9]CCCC)=[CH2:8].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:44]1[CH:52]=[CH:51][C:47]([C:48]([OH:50])=[O:49])=[C:46]([CH3:53])[CH:45]=1.Cl>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)CCC>[C:7]([C:44]1[CH:52]=[CH:51][C:47]([C:48]([OH:50])=[O:49])=[C:46]([CH3:53])[CH:45]=1)(=[O:9])[CH3:8]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
16.6 g (120 mmol) of potassium carbonate, 30.1 g (300 mmol) of n-butyl vinyl ether, 44.9 mg (0.2 mmol) of palladium acetate and 0.247 g (0.6 mmol) of 1,3-bis(diphenylphosphino)propane were added to a suspension solution of 21.5 g (100 mmol) of 4-bromo-2-methylbenzoic acid and 64.5 g of n-butanol. After degassing and nitrogen-purging inside of the reactor, the mixture was refluxed for 5 hours. After cooling the reaction solution to 80° C., n-butanol and n-butyl vinyl ether were distilled off under reduced pressure. After adding 172 g of toluene and 108 g of water, the mixture was neutralized by adding 15.6 g (150 mmol) of concentrated hydrochloric acid, and the water phase was separated. The obtained toluene solution was analyzed by a quantitative analysis method using HPLC. A content of 4-acetyl-2-methylbenzoic acid was 16.9 g (yield 95%).
Workup
- customAfter degassing
- customnitrogen-purging inside of the reactor
- temperaturethe mixture was refluxed for 5 hours
- distillationn-butanol and n-butyl vinyl ether were distilled off under reduced pressure
- additionAfter adding 172 g of toluene and 108 g of water
- customthe water phase was separated
Sources & evidence
- ORD record
- ord-dfe81019fdd04925934a5b580050f4b2
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952175B2
Reaction notes
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