Methanol → 4-Bromo-2,6-dimethylbenzoic acid

HRID 2427487

Reaction equation

HRID 2427487 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([C:6]#N)=[C:4]([CH3:11])[CH:3]=1.[OH-:12].[Na+].C[OH:15]>>[Br:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([C:6]([OH:15])=[O:12])=[C:4]([CH3:11])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 109107954-Bromo-2,6-dimethylbenzonitrile

Product 1

HCID 119590064-Bromo-2,6-dimethylbenzoic acid

Procedure

4-Bromo-2,6-dimethylbenzonitrile (4.0 g, 19 mmol) was stirred in MeOH (100 mL) and 5N NaOH (100 mL) at 100° C. for 12 hours. The reaction was cooled to room temperature and partitioned between CH2Cl2 and water and the organic layer was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the resulting product was stirred in H2PO3 (20 mL) for 6 hours at 150° C. The reaction mixture was basified with 6M KOH, filtered and then acidified with 12M HCl. The reaction was partitioned between CH2Cl2 and water and the organic layer was dried over anhydrous Na2-SO4. The solvent was removed under reduced pressure to afford the product (2.81 g). 1H NMR (300 MHz, CDCl3): δ 7.22 (s, 2H), 6.17 (s, 1H), 5.67 (s, 1H), 2.36 (s, 6H).

Workup

  1. custompartitioned between CH2Cl2 and water
  2. dry with materialthe organic layer was dried over anhydrous Na2SO4
  3. customThe solvent was removed under reduced pressure
  4. filtrationfiltered
  5. customThe reaction was partitioned between CH2Cl2 and water
  6. dry with materialthe organic layer was dried over anhydrous Na2-SO4
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a3950c17acdc46008ccc5aa9ae1ac61e
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Linked notes

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