2,4-Di-tert-pentylphenol → HCID 69287853, compound

HRID 2373107Notes

Reaction equation

HRID 2373107 reaction equation
[C:1]([C:6]1[CH:11]=[C:10]([C:12]([CH2:15][CH3:16])([CH3:14])[CH3:13])[CH:9]=[CH:8][C:7]=1[OH:17])([CH2:4][CH3:5])([CH3:3])[CH3:2].Br[C:19]1[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22]>N1C=CC=CC=1.C(OCC)C.[Cu]Cl>[C:1]([C:6]1[CH:11]=[C:10]([C:12]([CH2:15][CH3:16])([CH3:14])[CH3:13])[CH:9]=[CH:8][C:7]=1[O:17][C:19]1[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22])([CH2:4][CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 84552,4-Di-tert-pentylphenolHCID 11894Methyl 2-bromobenzoate

Product 1

HCID 69287853HCID 69287853, compound

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 1049PyridineSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

First, methyl 2,4-di-(tert-amyl)phenoxybenzoate was prepared. To a stirred suspension under argon of sodium hydride (60% dispersion in mineral oil, 1.1 g, 46.5 mmol, washed with ligroin to remove the oil) in pyridine (60 mL) was added dropwise a solution of 2,4-di-(tert-amyl)phenol (12.0 g, 51.2 mmol) in 20 mL of pyridine. The mixture was stirred for 2 h at room temperature and then treated dropwise with a solution of methyl 2-bromobenzoate (10 g, 46.5 mmol) in 10 mL of pyridine. Copper (I) chloride (1.15 g, 11.6 mmol) was added, and the mixture was heated at reflux 16 h and then cooled to ambient. The mixture was diluted with diethyl ether, washed successively with 10% aqueous HCl, water, and brine, and then dried over Na2SO4. The solvent was removed at reduced pressure to deposit dark brown oil. This crude product was purified by column chromatography to give 25.5 g, 78% of theory) of a light brown oil. 1H NMR (CDCl3): δ 0.70 (t, 6H), 1.3 (s, 6H), 1.4 (s, 6H), 1.63 (q, 2H), 1.85 (q, 2H), 3.85 (s, 3H), 6.68 (d, 1H), 6.82 (d, 1H), 7.05 (m, 2H), 7.3 (br s, 1H), 7.35 (t, 1H), 7.9 (dd, 1H).

Workup

  1. washTo a stirred suspension under argon of sodium hydride (60% dispersion in mineral oil, 1.1 g, 46.5 mmol, washed with ligroin
  2. customto remove the oil) in pyridine (60 mL)
  3. temperaturethe mixture was heated
  4. temperatureat reflux 16 h
  5. temperaturecooled
  6. washwashed successively with 10% aqueous HCl, water, and brine
  7. dry with materialdried over Na2SO4
  8. customThe solvent was removed at reduced pressure
  9. customThis crude product was purified by column chromatography
  10. customto give 25.5 g, 78% of theory) of a light brown oil

Sources & evidence

ORD record
ord-27b8facad628491fbf3ca836d7643140
Source dataset
uspto-grants-2008_12
Patent number
US07459263B2

Reaction notes

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