O-Cresol → 2-(2-Methylphenoxy)benzoic acid

HRID 1198617Notes

Reaction equation

HRID 1198617 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C1C=CC([I+][C:16]2[C:21]([C:22]([O-:24])=[O:23])=[CH:20][CH:19]=[CH:18][CH:17]=2)=CC=1>CO.[OH-].[Na+]>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:20]1[CH:19]=[CH:18][CH:17]=[CH:16][C:21]=1[C:22]([OH:24])=[O:23]

Participants

5

Reactant 2

HCID 335O-CresolHCID 73883Iodonium, (2-carboxyphenyl)phenyl-, inner salt

Product 1

HCID 2330382-(2-Methylphenoxy)benzoic acidYield 64.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 2-methylphenol (III: R3 =H) (33 g, 305 mmol) in MeOH (100 mL) was treated with Na (2.1 g, 90 mmol), and excess MeOH was removed under reduced pressure. Diphenyliodonium-2-carboxylate (II: R1 =H) (19.6 g, 60 mmol) and cupric acetate (0.5 g) were added and the mixture was stirred at 90° C. for 10 h. The solution was diluted with 2N NaOH, filtered through celite and acidified with HCl. The mixture was then dissolved in 2N K2CO3 and extracted twice with EtOAc to remove excess 2-methylphenol. The aqueous layer was then poured into excess 2N HCl to give 2-(2-methylphenoxy)benzoic acid (IV: R1 =R3 =H) (8.85 g, 64%), suitable for the next step. A sample crystallized from ligroin, mp 133°-134° C. (Ber, 1905, 38, 2111 records mp 133.5° C.).

Workup

  1. customwas removed under reduced pressure
  2. filtrationfiltered through celite
  3. dissolutionThe mixture was then dissolved in 2N K2CO3
  4. extractionextracted twice with EtOAc
  5. customto remove excess 2-methylphenol
  6. additionThe aqueous layer was then poured into excess 2N HCl

Sources & evidence

ORD record
ord-39e02fd31af6402a87b5b5a2da9f82e4
Source dataset
uspto-grants-1994_01
Patent number
US05281620

Reaction notes

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