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

HRID 602011Notes

Reaction equation

HRID 602011 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 15% aqueous sodium hydroxide solution and the mixture obtained was stirred at 50° C. for 4 hours. Then, the reaction mixture was added to hydrochloric acid for acidification. Crystals precipitated were collected by filtration and dried to obtain 13.0 g of 4-(2-propynyloxy)-3,5-dimethoxybenzoic acid represented by the formula:

Workup

  1. customthe mixture obtained
  2. customCrystals precipitated
  3. filtrationwere collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-369256f9b4064cc5b485a8c3f3d056d7
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Reaction notes

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