HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Potassium Carbonate → 7-(2-m-Tolyl-ethoxy)-benzo[1,3]dioxole-5-carboxylic Acid 2-m-tolyl-ethyl Ester

HRID 1918334
Notes
Print preview

Reaction equation

HRID 1918334 reaction equation
[OH:1][C:2]1[C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=[C:4]([C:11]([OH:13])=[O:12])[CH:3]=1.Br[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:19]1([CH3:23])[CH:20]=[CH:21][CH:22]=[C:17]([CH2:16][CH2:15][O:12][C:11]([C:4]2[CH:3]=[C:2]([O:1][CH2:15][CH2:16][C:17]3[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=3)[C:7]3[O:8][CH2:9][O:10][C:6]=3[CH:5]=2)=[O:13])[CH:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 5706841-(2-Bromoethyl)-3-methylbenzene2×HCID 220524917-Hydroxy-1,3-benzodioxole-5-carboxylic acid

Product 1

HCID 671703457-(2-m-Tolyl-ethoxy)-benzo[1,3]dioxole-5-carboxylic Acid 2-m-tolyl-ethyl EsterYield 78.3%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
90 °C

Procedure

2.5 g of 7-hydroxy-benzo[1,3]dioxole-5-carboxylic acid, 6.8 g of 1-(2-bromo-ethyl)-3-methyl-benzene and 7.6 g of potassium carbonate were stirred in 100 ml of anhydrous DMF for 10 h at 80° C. Then another 1.4 g of 1-(2-bromo-ethyl)-3-methyl-benzene and 1.5 g of potassium carbonate were added and the mixture was stirred for 5 h at 90° C. The solvent was removed in vacuo and the residue dissolved in 200 ml of water and 200 ml of EA. The organic layer was separated, washed with 100 ml of a saturated aqueous sodium carbonate solution, dried with magnesium sulfate and evaporated to yield 4.5 g of the title compound.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in 200 ml of water
  3. customThe organic layer was separated
  4. washwashed with 100 ml of a saturated aqueous sodium carbonate solution
  5. dry with materialdried with magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-815eaa6f7c864670a42d42630158ea6b
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08618304B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes