Acetic Acid → 2,6-Ditert-butyl-4-[(4-methoxyphenyl)methyl]phenol

HRID 66629Notes

Reaction equation

HRID 66629 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]O)=[CH:20][CH:19]=1.C(O)=O.C(O)(=O)C>O>[C:11]([C:7]1[CH:8]=[C:9]([CH2:22][C:21]2[CH:24]=[CH:25][C:18]([O:17][CH3:16])=[CH:19][CH:20]=2)[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:15])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 284Formic AcidHCID 77384-Methoxybenzyl alcoholHCID 314052,6-Di-tert-butylphenol

Product 1

HCID 3311942,6-Ditert-butyl-4-[(4-methoxyphenyl)methyl]phenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,6-Di-t-butyl-4-(4-methoxybenzyl) phenol was prepared as described for A above. A mixture of 2,6-di-t-butylphenol (51.5 g), 4-methoxybenzyl alcohol (34.5 g), formic acid (100 ml) and acetic acid (100 ml) was refluxed for 5 hours, diluted with water, and extracted with chloroform. Evaporation of the chloroform gave an oil which crystallized. Recrystallization from methanol gave colorless needles, mp 139° (58 g); (Found: C, 80.7; H, 9.30. Calc. for C22H30O2 : C, 80.9; H, 9.26%); pmr spectrum: δ1.42, 18H, S; δ3.79, 3H, S; δ3.86, 2H, S; δ5.04, 1H, S; δ6.83, 2H, D (J=8 Hz); δ6.98, 2H, S; δ7.12, 2H, D (J=8 Hz).

Workup

  1. temperaturewas refluxed for 5 hours
  2. extractionextracted with chloroform
  3. customEvaporation of the chloroform
  4. customgave an oil which
  5. customcrystallized
  6. customRecrystallization from methanol
  7. customgave colorless needles, mp 139° (58 g)

Sources & evidence

ORD record
ord-772af91edb354582a0e1ec9492fcf929
Source dataset
uspto-grants-1982_08
Patent number
US04342777

Reaction notes

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