Dimethylformamide → 2-Propynyl 4-(2-propynyloxy)-3-methoxybenzoate

HRID 602013Notes

Reaction equation

HRID 602013 reaction equation
CN(C=O)C.[OH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[O:16][CH3:17].[CH2:18](Br)[C:19]#[CH:20].[C:22](=O)([O-])[O-].[K+].[K+].C(O[CH2:32][CH3:33])(=O)C>>[CH2:18]([O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([O:13][CH2:22][C:32]#[CH:33])=[O:12])=[CH:9][C:8]=1[O:16][CH3:17])[C:19]#[CH:20]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 7842Propargyl bromideHCID 8468Vanillic AcidHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate

Product 1

HCID 593017652-Propynyl 4-(2-propynyloxy)-3-methoxybenzoate

Conditions

Temperature
80 °C

Procedure

To 100 ml of DMF were added 10 g of 4-hydroxy-3-methoxybenzoic acid, 15.7 g of propargyl bromide and 18 g of potassium carbonate, and the mixture obtained was stirred at room temperature for 8 hours and at 80° C. for 2 hours. Then, ethyl acetate was added to the reaction mixture and the mixture was filtered through Celite. Water and dilute hydrochloric acid were added to the filtrate in order and it was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The crystals obtained were washed with a mix solvent of hexane and MTBE to obtain 13.2 g of 2-propynyl 4-(2-propynyloxy)-3-methoxybenzoate represented by the formula:

Workup

  1. customthe mixture obtained
  2. filtrationthe mixture was filtered through Celite
  3. additionWater and dilute hydrochloric acid were added to the filtrate in order and it
  4. extractionwas extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crystals obtained
  8. washwere washed with a mix solvent of hexane and MTBE

Sources & evidence

ORD record
ord-0822bfeaf9ab468b9038284801dbd196
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Reaction notes

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