Oxalic Acid → 2,4-Bis(1,1-dimethylethyl)-6-((4-methoxyphenyl)methyl)phenol

HRID 66627

반응식

HRID 66627 반응식
[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.C(O)(=O)C(O)=O>C(O)(=O)C.O>[C:11]([C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]([OH:15])=[C:7]([CH2:22][C:21]2[CH:24]=[CH:25][C:18]([O:17][CH3:16])=[CH:19][CH:20]=2)[CH:8]=1)([CH3:14])([CH3:13])[CH3:12]

참가 물질

6

반응물 3

HCID 971Oxalic AcidHCID 73112,4-Di-tert-butylphenolHCID 77384-Methoxybenzyl alcohol

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매2회

실험 절차

4,6-Di-t-butyl-2-(4-methoxybenzyl) phenol was prepared as follows: A solution of 2,4-di-t-butylphenol (57.5 g), 4-methoxybenzyl alcohol (34.5 g) and oxalic acid (2 g) in acetic acid (80 ml) and water (2 ml) was refluxed for 7 hours, diluted with water, and extracted with chloroform. Distillation of the chloroform extract gave an oil (b.p. 200°-210° C. at 2 mm Hg) which crystallized (58 g; 71.4%). The product was recrystallized from methanol to give glistening colorless needles, m.p. 84°-85°; (Found: C, 81.0; H, 9.21. Calc. for C22H30O2 : C, 80.9; H, 9.26%). The pmr spectrum exhibited the following: δ1.30, 9H, S; δ1.38, 9H, S; δ3.79, 3H, S; δ3.83, 2H, S; δ4.62, 1H, S; δ6.84, 2H, D (J=8 Hz); δ7.02, 1H, D (J=2 Hz); δ7.14, 2H, D (J=8 Hz); δ7.23, 1H, D (J=Hz).

후처리

  1. extractionextracted with chloroform
  2. distillationDistillation of the chloroform
  3. extractionextract
  4. customgave an oil (b.p. 200°-210° C. at 2 mm Hg) which
  5. customcrystallized (58 g; 71.4%)
  6. customThe product was recrystallized from methanol
  7. customto give

출처 및 근거

ORD 기록
ord-f3d4554a5ec14857b1090dad77949019
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04342777

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