Potassium Carbonate → HCID 67170345, compound

HRID 1475745Notes

Reaction equation

HRID 1475745 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

Participants

5

Reactant 3

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

Product 1

HCID 67170345HCID 67170345, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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-32063fa5b46a4ade8a507a9fd20ff423
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

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