Hydrochloric Acid → 5-(2,4-Dichlorophenyl)-3-methylpenta-2,4-dienoic acid

HRID 597893Notes

Reaction equation

HRID 597893 reaction equation
C([O:3][C:4](=[O:18])[CH:5]=[C:6]([CH3:17])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16])C.CO.[OH-].[Na+].Cl>C1COCC1.O>[Cl:16][C:10]1[CH:11]=[C:12]([Cl:15])[CH:13]=[CH:14][C:9]=1[CH:8]=[CH:7][C:6]([CH3:17])=[CH:5][C:4]([OH:18])=[O:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 724732465-(2,4-Dichlorophenyl)-3-methylpenta-2,4-dienoic acid ethyl ester

Product 1

HCID 727406815-(2,4-Dichlorophenyl)-3-methylpenta-2,4-dienoic acidYield 89.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

5-(2,4-Dichlorophenyl)-3-methylpenta-2,4-dienoic acid ethyl ester (5 g, 0.0184 mol) was dissolved in THF (125 mL). Water (50 mL), MeOH (50 mL), and NaOH (18.44 mL of a 2M solution in water, 2 eq) were then added. After 6 hours, TLC analysis showed complete conversion of the starting materials and the mixture was acidified to pH 1 by addition of 6N HCl. The resulting solid was collected to give 4.24 g of 5-(2,4-dichlorophenyl)-3-methylpenta-2,4-dienoic acid.

Workup

  1. customThe resulting solid was collected

Sources & evidence

ORD record
ord-9d0519cf18e14e2d8941badd9e5c80f1
Source dataset
uspto-grants-2011_03
Patent number
US07897601B2

Reaction notes

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