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Water → 7-(2-m-Tolyl-ethoxy)-benzo[1,3]dioxole-5-carboxylic Acid

HRID 1475746
Notes
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Reaction equation

HRID 1475746 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]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 671703457-(2-m-Tolyl-ethoxy)-benzo[1,3]dioxole-5-carboxylic Acid 2-m-tolyl-ethyl Ester

Product 1

HCID 671702937-(2-m-Tolyl-ethoxy)-benzo[1,3]dioxole-5-carboxylic AcidYield 96%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

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

  1. customevaporated
  2. dissolutionThe residue was dissolved in 300 ml of a 0.1 M aqueous solution of sodium hydroxide
  3. washwashed three times with 50 ml each of diisopropyl ether
  4. stirringthe mixture stirred for 30 min at room temperature
  5. filtrationThe product was collected by filtration
  6. washwashed
  7. customdried in vacuo

Sources & evidence

ORD record
ord-92ecb827f70f4adf8c7660d74bd05f36
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09018383B2

Reaction notes

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