Resorcinol → 3-(4-Methylcyclohexyloxy)phenol

HRID 871181

반응식

HRID 871181 반응식
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[CH3:9][CH:10]1[CH2:15][CH2:14][CH:13](O)[CH2:12][CH2:11]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH3:9][CH:10]1[CH2:15][CH2:14][CH:13]([O:2][C:1]2[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][CH:8]=2)[CH2:12][CH2:11]1

참가 물질

6

반응물 4

HCID 5054ResorcinolHCID 115244-MethylcyclohexanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylate

생성물 1

HCID 126671573-(4-Methylcyclohexyloxy)phenol수율 22%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

In a four necked flask (2 L) sufficiently dried, substituted with nitrogen, and equipped with a dropping funnel, Dimroth condenser tube, thermometer and stirring blade, resorcinol (110 g, 1.0 mol), 4-methylcyclohexanol (114 g, 1.0 mol) and triphenylphosphine (393 g, 1.5 mol) were dissolved in dried tetrahydrofuran (500 ml) under a nitrogen gas stream, and a mixed solution of diisopropyl azodicarboxylate (269 g, 1.3 mol) and dried tetrahydrofuran (400 ml) was dropped for 1 hour while cooling with iced saline solution. Next, it was stirred at room temperature for 12 hours. After the reaction terminated, 30% hydrogen peroxide (200 ml) was dropped through the dropping funnel for 10 minutes, then the reaction solution was dissolved in 2 L toluene, and washed three times with 1 L water. Toluene was distilled away by evaporation, and the residue was purified by column chromatography using hexane and ethyl acetate as developing solvents, to obtain a red brown objective product (hereinafter, referred to as R-2A) (45.0 g, 22% yield, 97% GC purity).

후처리

  1. customIn a four necked flask (2 L) sufficiently dried
  2. customequipped with a dropping funnel, Dimroth condenser tube
  3. temperaturewhile cooling with iced saline solution
  4. customAfter the reaction terminated
  5. addition30% hydrogen peroxide (200 ml) was dropped through the dropping funnel for 10 minutes
  6. dissolutionthe reaction solution was dissolved in 2 L toluene
  7. washwashed three times with 1 L water
  8. distillationToluene was distilled away by evaporation
  9. customthe residue was purified by column chromatography
  10. customto obtain a red brown objective product (hereinafter,

출처 및 근거

ORD 기록
ord-d1bc435a8ccf490787d502afc68e95e0
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969629B2

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