Sodium Hydroxide → 2-(2',3'-Dichloro[1,1'-biphenyl]-3-yl)propanedioic acid

HRID 1502594Notes

Reaction equation

HRID 1502594 reaction equation
C([O:3][C:4](=[O:25])[CH:5]([C:11]1[CH:12]=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=2[Cl:24])[CH:14]=[CH:15][CH:16]=1)[C:6]([O:8]CC)=[O:7])C.[OH-].[Na+]>>[Cl:24][C:18]1[C:19]([Cl:23])=[CH:20][CH:21]=[CH:22][C:17]=1[C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([CH:5]([C:4]([OH:25])=[O:3])[C:6]([OH:8])=[O:7])[CH:12]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 669733992-(2',3'-Dichloro-[1,1'-biphenyl]-3-yl)propanedioic acid 1,3-diethyl ester2×

Product 1

HCID 669736132-(2',3'-Dichloro[1,1'-biphenyl]-3-yl)propanedioic acid

Conditions

Temperature
70 °C

Procedure

2-(2′,3′-Dichloro-[1,1′-biphenyl]-3-yl)propanedioic acid 1,3-diethyl ester (i.e. the product of Step B, 0.30 g, 0.79 mmol) was added to 2% aqueous sodium hydroxide (5 mL), and the reaction mixture was heated at 70° C. for 20 min. The reaction mixture was cooled, quenched with 6 N aqueous hydrochloric acid, and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to yield the title compound (0.20 g).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customquenched with 6 N aqueous hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8f42987e55ae46eba333ecf240453a94
Source dataset
uspto-grants-2015_12
Patent number
US09210932B2

Reaction notes

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