Hydrochloric Acid → 3-Methoxy-4-(prop-2-ynyloxy)benzoic acid

HRID 1675570Notes

Reaction equation

HRID 1675570 reaction equation
[CH2:1]([O:4][C:5]1[CH:16]=[CH:15][C:8]([C:9]([O:11]CC#C)=[O:10])=[CH:7][C:6]=1[O:17][CH3:18])[C:2]#[CH:3].[OH-].[Na+].Cl>CO>[CH2:1]([O:4][C:5]1[CH:16]=[CH:15][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[O:17][CH3:18])[C:2]#[CH:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 593017652-Propynyl 4-(2-propynyloxy)-3-methoxybenzoate

Product 1

HCID 131214803-Methoxy-4-(prop-2-ynyloxy)benzoic acidYield 107.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 50 ml of methanol were added 13.2 g of 2-propynyl 4-(2-propynyloxy)-3-methoxybenzoate and 40 ml of a 15% aqueous sodium hydroxide solution, and the resulting mixture was stirred at room temperature for 8 hours, and then at 50° C. for 2 hours. Thereafter, the reaction mixture which had been allowed to cool to near room temperature was added to hydrochloric acid to make the mixture acidic. The precipitated crystals were collected by filtration, and dried, and 12.0 g of 4-(2-propynyloxy)-3-methoxybenzoic acid was obtained.

Workup

  1. waitat 50° C. for 2 hours
  2. temperatureto cool to near room temperature
  3. filtrationThe precipitated crystals were collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-dadb5c4102d040e59fa5bc8703307617
Source dataset
uspto-grants-2011_08
Patent number
US08003699B2

Reaction notes

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