Lithium Hydroxide → m-Phenylenediacetic acid

HRID 977179Notes

Reaction equation

HRID 977179 reaction equation
C[C:2](C)([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12](O)=O)[CH:7]=1)[C:3]([OH:5])=[O:4].[OH-:16].[Li+].[O:18]1[CH2:22]CCC1>>[C:22]([CH2:12][C:8]1[CH:7]=[C:6]([CH2:2][C:3]([OH:5])=[O:4])[CH:11]=[CH:10][CH:9]=1)([OH:18])=[O:16]

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 19965411HCID 19965411, compound

Product 1

HCID 29788m-Phenylenediacetic acid

Procedure

Dimethyl-3-carboxyphenyl acetic acid (870 mg) in 10 ml tetrahydrofuran was treated with lithium hydroxide (8.5 ml, 0.5M solution) at 0° C. After stirring at room temperature for 4 h, all solvent was evaporated, and the residue partitioned between saturated sodium hydrogen carbonate and ethyl acetate. The aqueous layer was separated, acidified (1N HCl) and extracted with dichloromethane (2×25 ml). The combined organic layers were dried (MgSO4) and solvent removed to leave 3-(carboxymethyl)phenyl acetic acid, mp 96°-98° C.

Workup

  1. customall solvent was evaporated
  2. customthe residue partitioned between saturated sodium hydrogen carbonate and ethyl acetate
  3. customThe aqueous layer was separated
  4. extractionextracted with dichloromethane (2×25 ml)
  5. dry with materialThe combined organic layers were dried (MgSO4) and solvent
  6. customremoved

Sources & evidence

ORD record
ord-0aa6e2b346024be8a9f844faa65ebefd
Source dataset
uspto-grants-1997_03
Patent number
US05614532

Reaction notes

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