Ethanol → HCID 69286285, compound

HRID 2373108Notes

Reaction equation

HRID 2373108 reaction equation
[C:1]([C:6]1[CH:22]=[C:21]([C:23]([CH2:26][CH3:27])([CH3:25])[CH3:24])[CH:20]=[CH:19][C:7]=1[O:8][C:9]1[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([O:13]C)=[O:12])([CH2:4][CH3:5])([CH3:3])[CH3:2].[OH-].[K+].C(O)C>C(OCC)C>[C:1]([C:6]1[CH:22]=[C:21]([C:23]([CH2:26][CH3:27])([CH3:25])[CH3:24])[CH:20]=[CH:19][C:7]=1[O:8][C:9]1[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([OH:13])=[O:12])([CH2:4][CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 69287853HCID 69287853, compound

Product 1

HCID 69286285HCID 69286285, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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).

Workup

  1. customNext 2,4-di-(tert-amyl)phenoxybenzoic acid was prepared
  2. temperaturewas heated
  3. temperatureat reflux for 4 h
  4. temperaturecooled
  5. washthe mixture was washed twice with 10% aqueous HCl
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. customthe solvent was removed at reduced pressure
  8. customThis crude product was purified by recrystallization from heptane

Sources & evidence

ORD record
ord-75b51aae8e8d4272b4580c5502570f52
Source dataset
uspto-grants-2008_12
Patent number
US07459263B2

Reaction notes

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