Hydrochloric Acid → 2-(3,4-Dichlorophenyl)-2-methylpropanoic acid

HRID 1868796Notes

Reaction equation

HRID 1868796 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([CH3:15])([CH3:14])[C:10]([O:12]C)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].C1COCC1.O.O.[OH-].[Li+].Cl>C(OCC)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([CH3:15])([CH3:14])[C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 20314623HCID 20314623, compoundHCID 21881883Oxolane--water (1/1)

Product 1

HCID 155826452-(3,4-Dichlorophenyl)-2-methylpropanoic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

To methyl 2-(3,4-dichlorophenyl)-2-methylpropanoate (22.03 g, 89.1 mmol) was added THF/water (4:1) (178 mL) and lithium hydroxide hydrate (22.4 g, 535 mmol). The reaction was then stirred at 50° C. for 3 days. The reaction mixture was acidified with 3N HCl, diluted with 200 mL of diethyl ether, added to a separatory funnel, partitioned with water, washed 2 times with 100 mL of water, separated, dried over Na2SO4, and concentrated in vacuo to give the title compound which was used without further purification. MS (m/z)=233 (M+H)+.

Workup

  1. additionadded to a separatory funnel
  2. custompartitioned with water
  3. washwashed 2 times with 100 mL of water
  4. customseparated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-211fd79158004438a73e46c7c28cc638
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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