Water → 7-(2-m-Tolyl-ethoxy)-benzo[1,3]dioxole-5-carboxylic Acid
Reaction equation
C1(C)C=CC=C(CC[O:9][C:10]([C:12]2[CH:20]=[C:19]([O:21][CH2:22][CH2:23][C:24]3[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=3)[C:15]3[O:16][CH2:17][O:18][C:14]=3[CH:13]=2)=[O:11])C=1.[OH-].[Na+].C1COCC1.O>CO>[C:26]1([CH3:30])[CH:27]=[CH:28][CH:29]=[C:24]([CH2:23][CH2:22][O:21][C:19]2[C:15]3[O:16][CH2:17][O:18][C:14]=3[CH:13]=[C:12]([C:10]([OH:11])=[O:9])[CH:20]=2)[CH:25]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
4.5 g of 7-(2-m-tolyl-ethoxy)-benzo[1,3]dioxole-5-carboxylic acid 2-m-tolyl-ethyl ester and 650 mg of sodium hydroxide were dissolved in 50 ml of methanol, 50 ml of THF and 5 ml of water. The mixture was kept at room temperature for 20 h, then stirred at 50° C. for 5 h and evaporated. The residue was dissolved in 300 ml of a 0.1 M aqueous solution of sodium hydroxide and washed three times with 50 ml each of diisopropyl ether. The pH was adjusted to 2 with sodium hydrogensulfate and the mixture stirred for 30 min at room temperature. The product was collected by filtration, washed and dried in vacuo to yield 3.1 g of the title compound.
Workup
- customevaporated
- dissolutionThe residue was dissolved in 300 ml of a 0.1 M aqueous solution of sodium hydroxide
- washwashed three times with 50 ml each of diisopropyl ether
- stirringthe mixture stirred for 30 min at room temperature
- filtrationThe product was collected by filtration
- washwashed
- customdried in vacuo
Sources & evidence
- ORD record
- ord-e28cc4705674484c91925bc6e53ecd91
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618304B2
Reaction notes
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