2,4-Di-tert-butylphenol → 2,4-Bis(1,1-dimethylethyl)-6-((4-methoxyphenyl)methyl)phenol

HRID 1074439Notes

Reaction equation

HRID 1074439 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][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>P(O)(O)O.C1(C)C=CC=CC=1>[CH3:2][C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([CH2:22][C:21]2[CH:24]=[CH:25][C:18]([O:17][CH3:16])=[CH:19][CH:20]=2)[C:6]=1[OH:15])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 73112,4-Di-tert-butylphenolHCID 77384-Methoxybenzyl alcohol

Product 1

HCID 1005772,4-Bis(1,1-dimethylethyl)-6-((4-methoxyphenyl)methyl)phenol

Reagents, catalysts & solvents 2

HCID 107909Phosphorous acidCatalystHCID 1140TolueneSolvent2×

Procedure

A mixture of 2,4-di-t-butylphenol (41.2 g), phosphorous acid (2 drops) and toluene (5 ml) was heated to 180°-200° in a three-necked flask fitted with a Dean-Stark trap containing toluene. 4-Methoxybenzyl alcohol (27.6 g) was melted and added in a slow stream to the mixture during 45 min. Heating was continued for a further 15 min by which time the theoretical amount of water (3.6 ml) had distilled. The reaction mixture was then distilled under pressure to give a pale yellow oil which rapidly crystallized. Recrystalization from methanol yielded colorless needless, m.p. and mixed m.p. with authentic material, 84°-85°; yield 59.3 g (91%). Found: C,80.9;H,9.26; calc for C,22H30O2 :C,81.0;H,9.21); 1Hmmr spectrum: δ1.30,9H,S; δ1.38,9H,S; δ3.79,3H,S; δ3.83,2H,S; δ4.61,H,S; δ6.84,2H,D(J=8 Hz); δ7.03, 1H,D(J=2 Hz); δ7.14,2H,D(J=8 Hz); δ7.23,1H,D(J=2 Hz).

Workup

  1. temperaturewas heated to 180°-200° in a three-necked flask
  2. customfitted with a Dean-Stark trap
  3. additionadded in a slow stream to the mixture during 45 min
  4. temperatureHeating
  5. distillationthe theoretical amount of water (3.6 ml) had distilled
  6. distillationThe reaction mixture was then distilled under pressure
  7. customto give a pale yellow oil which
  8. customrapidly crystallized
  9. customRecrystalization from methanol yielded colorless needless
  10. additionand mixed m.p. with authentic material, 84°-85°

Sources & evidence

ORD record
ord-176f5ce27c984b47b3edb0fd056f4eac
Source dataset
uspto-grants-1983_07
Patent number
US04391828

Reaction notes

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