Hydrochloric Acid → 5-(1,3-Benzodioxol-5-yl)-2,4-pentadienoic acid

HRID 652959Notes

Reaction equation

HRID 652959 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]=[CH:11][CH:12]=[CH:13][C:14]([O:16]CC)=[O:15])=[CH:4][C:3]=2[O:2]1.[OH-].[Na+].O.Cl>CO.O.CO>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]=[CH:11][CH:12]=[CH:13][C:14]([OH:16])=[O:15])=[CH:4][C:3]=2[O:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 54007855Ethyl 5-(2H-1,3-benzodioxol-5-yl)penta-2,4-dienoate

Product 1

HCID 943055-(1,3-Benzodioxol-5-yl)-2,4-pentadienoic acidYield 90.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of 6.8 g (27.6 mmol) of the ester compound prepared above in methanol (20 ml) was added in an argon atmosphere a solution of 11.0 g (275 mmol) of sodium hydroxide in water - methanol (1 : 6, 280 ml). The mixture was reacted at room temperature for 4.5 hours. Water was added to the reaction solution, followed by adjustment of the pH with 6N-hydrochloric acid to 3. Crystals then precipitated were isolated by filtration. There was obtained 5.478 g (25.1 mmol) of 5-(3,4-methylenedioxyphenyl)-2,4-pentadienic acid.

Workup

  1. customThe mixture was reacted at room temperature for 4.5 hours
  2. customCrystals then precipitated
  3. customwere isolated by filtration

Sources & evidence

ORD record
ord-ff4cdebb4d38459688177ebcbe3a6358
Source dataset
uspto-grants-1987_06
Patent number
US04673684

Reaction notes

Loading…