Hydrochloric Acid → 3,5-Dimethoxy-4-[(prop-2-yn-1-yl)oxy]benzoic acid

HRID 1675567Notes

Reaction equation

HRID 1675567 reaction equation
[CH2:1]([O:4][C:5]1[C:16]([O:17][CH3:18])=[CH:15][C:8]([C:9]([O:11]CC#C)=[O:10])=[CH:7][C:6]=1[O:19][CH3:20])[C:2]#[CH:3].[OH-].[Na+].Cl>CO>[CH2:1]([O:4][C:5]1[C:6]([O:19][CH3:20])=[CH:7][C:8]([C:9]([OH:11])=[O:10])=[CH:15][C:16]=1[O:17][CH3:18])[C:2]#[CH:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 593017922-Propynyl 4-(2-propynyloxy)-3,5-dimethoxybenzoate

Product 1

HCID 131214813,5-Dimethoxy-4-[(prop-2-yn-1-yl)oxy]benzoic acidYield 97.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To 50 ml of methanol were added 15.5 g of 2-propynyl 4-(2-propynyloxy)-3,5-dimethoxybenzoate and 40 ml of a 15% aqueous sodium hydroxide solution, and the resulting mixture was stirred at 50° C. for 4 hours. Thereafter, the reaction mixture which had been allowed to cool to near room temperature was made acidic by addition of hydrochloric acid. The precipitated crystals were collected by filtration, and dried, and 13.0 g of 4-(2-propynyloxy)-3,5-dimethoxybenzoic acid was obtained.

Workup

  1. temperatureto cool to near room temperature
  2. filtrationThe precipitated crystals were collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-90fc2e508923459780678596902922f9
Source dataset
uspto-grants-2011_08
Patent number
US08003699B2

Reaction notes

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