Hydrochloric Acid → HCID 15491035, compound

HRID 362837Notes

Reaction equation

HRID 362837 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH:10]([C:16]([O:18]CC)=[O:17])[C:11]([O:13]CC)=[O:12].[OH-].[K+].Cl>C(O)C.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH:10]([C:16]([OH:18])=[O:17])[C:11]([OH:13])=[O:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium Hydroxide2×HCID 23293631HCID 23293631, compound

Product 1

HCID 15491035HCID 15491035, compoundYield 101.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of diethyl 2-(2-(2-fluorophenyl)ethyl)malonate (381.8 g, 1.35 mol) and potassium hydroxide (227.3 g, 4.1 mol) and potassium hydroxide (227.3 g, 4.1 mol) in ethanol (500 mL) and water (500 mL) was refluxed for 24 h. The reaction mixture was placed in an ice bath and hydrochloric acid (6N, 442 mL) was added. The ethanol was removed in vacuo and the aqueous residue was extracted with diethyl ether. The extracts were dried (MgSO4) and concentrated in vacuo to give 309.3 g (100%) of 2-(2-(2-fluorophenyl)ethyl)malonic acid as an off-white solid. This product was used without further purification. NMR (DMSO-d6): d 6.8-6.2 (m, 4H, ArH), 2.4 (t, 1H, CH), 1.9 (q, 2H, CH2), 1.3 (t, 2H, CH2). IR (KBr) 1691 CM-1.

Workup

  1. temperaturewas refluxed for 24 h
  2. customThe reaction mixture was placed in an ice bath
  3. customThe ethanol was removed in vacuo
  4. extractionthe aqueous residue was extracted with diethyl ether
  5. dry with materialThe extracts were dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-402a8da2f55a4e649c5d778afd115400
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

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