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

HRID 1074439

反応式

HRID 1074439 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 107909Phosphorous acid触媒HCID 1140Toluene溶媒2 回

実験手順

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).

後処理

  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°

出典と根拠

ORDレコード
ord-176f5ce27c984b47b3edb0fd056f4eac
出典データセット
uspto-grants-1983_07
特許番号
US04391828

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