Sodium Hydroxide → 2,5-Dimethylphenylacetic acid
Reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].ClCC1([C:16]2[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=2[CH3:23])OCC(C)(C)CO1.[OH-].[Na+]>C(O)CO.O>[CH3:23][C:17]1[CH:18]=[CH:19][C:20]([CH3:22])=[CH:21][C:16]=1[CH2:2][C:1]([OH:4])=[O:3]Participants
Conditions
- Temperature
- 182.5 °C
Procedure
A mixture of 4.1 g [0.05 mol] of sodium acetate and 10.75 g [0.04 mol] of 2-chloromethyl-5,5-dimethyl-2-(2,5-dimethylphenyl)-[1,3]dioxane in 50 ml of ethylene glycol is heated at 180 to 185° C. for 5 hours. It is then allowed to cool to 90 to 95° C., 20 ml of 30% strength sodium hydroxide solution are added, and the mixture is heated at 100 to 105° C. for 1 hour. The reaction mixture is diluted with 80 ml of water at room temperature and extracted twice with 10 ml of methylene chloride each time. The aqueous phase is then adjusted to pH 1 with conc. hydrochloric acid, and the solid is filtered off with suction, washed twice with 20 ml of water each time and dried. 6.20 g of white solid are obtained with a purity of 99.3% (GC). The yield is thus 93.7% of theory.
Workup
- temperatureto cool to 90 to 95° C.
- temperaturethe mixture is heated at 100 to 105° C. for 1 hour
- extractionextracted twice with 10 ml of methylene chloride each time
- filtrationthe solid is filtered off with suction
- washwashed twice with 20 ml of water each time
- customdried
Sources & evidence
- ORD record
- ord-9fa6968bc5d54b928f46cc32d49d4f6e
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07629476B2
Reaction notes
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