Reaction #2460290

Reaction equation

methyl 2,4-di-(tert-amyl)phenoxybenzoate

potassium hydroxide

ethanol

→

2,4-di-(tert-amyl)phenoxybenzoic acid

Solvents

Diethyl ether

Conditions

Workup

1. 1
   OtherNext 2,4-di-(tert-amyl)phenoxybenzoic acid was prepared
2. 2
   Temperaturewas heated
3. 3
   Temperatureat reflux for 4 h
4. 4
   Temperaturecooled
5. 5
   Washthe mixture was washed twice with 10% aqueous HCl
6. 6
   DryingThe organic layer was dried (Na2SO4)
7. 7
   Otherthe solvent was removed at reduced pressure
8. 8
   OtherThis crude product was purified by recrystallization from heptane

Procedure

Next 2,4-di-(tert-amyl)phenoxybenzoic acid was prepared. A mixture of methyl 2,4-di-(tert-amyl)phenoxybenzoate (7.44 g, 20 mmol), potassium hydroxide (2.3 g, 40 mmol), and ethanol (60 mL) was heated at reflux for 4 h and then cooled to ambient. Diethyl ether (20 mL) was added, and the mixture was washed twice with 10% aqueous HCl. The organic layer was dried (Na2SO4) and the solvent was removed at reduced pressure to deposit a yellow solid. This crude product was purified by recrystallization from heptane to provide 5.0 g, 70% of theory) of 2,4-di-(tert-amyl)phenoxybenzoic acid as a tan solid. 1H NMR (CDCl3): δ 0.75 (t, 6H), 1.3 (s, 6H), 1.4 (s, 6H), 1.65 (q, 2H), 1.80 (q, 2H), 3.85 (s, 3H), 6.80 (d, 2H), 7.15 (m, 2H), 7.35(br s, 1H), 7.45 (t, 1H), 8.2 (d, 1H).

Source