Hydrochloric Acid → (2-Hydroxy-3-t-butyl-5-methylphenyl)-(2-hydroxy-4-t-butylphenyl)methane

HRID 727459

반응식

HRID 727459 반응식
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:5][C:4]=1[OH:13].[C:14]([C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=1[OH:25])([CH3:17])([CH3:16])[CH3:15].[OH-].[Na+].Cl>O>[OH:25][C:19]1[C:18]([C:14]([CH3:16])([CH3:15])[CH3:17])=[CH:23][C:22]([CH3:24])=[CH:21][C:20]=1[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:5][C:4]=1[OH:13]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 170042-tert-Butyl-4-methylphenolHCID 196902415-(tert-Butyl)-2-(hydroxymethyl)phenol

생성물 1

HCID 19706004(2-Hydroxy-3-t-butyl-5-methylphenyl)-(2-hydroxy-4-t-butylphenyl)methane수율 36%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

In a 300 ml eggplant-type flask equipped with a Dimroth condenser, 10.3 g (0.057 mol) of intermediate 2-(hydroxymethyl)-5-t-butylphenol and 10.2 g (0.062 mol) of 2-t-butyl-4-methylphenol were suspended in 60 ml of water. To this suspension, an aqueous solution having 10.2 g (0.26 mol) of sodium hydroxide dissolved in 50 ml of water, was added, and the mixture was stirred by a magnetic stirrer. This mixture was heated to a temperature of from 100° to 110° C. and stirred at that temperature for 17.5 hours. The reaction mixture was cooled to room temperature, acidified by concentrated hydrochloric acid and then extracted with ethyl acetate. The obtained ethyl acetate solution was washed with water and then dried over anhydrous magnesium sulfate. From the solution having the anhydrous magnesium sulfate removed, ethyl acetate was distilled off, and the obtained residue was roughly separated by silica gel column chromatography. To the obtained brown highly viscous oil, n-hexane was added and left to stand still to obtain 6.7 g (0.021 mol, yield: 36.0%) of (2-hydroxy-3-t-butyl-5-methylphenyl)-(2-hydroxy-4-t-butylphenyl)methane as a white solid. By 1HNMR, this solid was confirmed to be the desired product.

후처리

  1. additionwas added
  2. temperatureThis mixture was heated to a temperature of from 100° to 110° C.
  3. stirringstirred at that temperature for 17.5 hours
  4. extractionextracted with ethyl acetate
  5. washThe obtained ethyl acetate solution was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customremoved
  8. distillationethyl acetate was distilled off
  9. customthe obtained residue was roughly separated by silica gel column chromatography
  10. additionTo the obtained brown highly viscous oil, n-hexane was added
  11. waitleft

출처 및 근거

ORD 기록
ord-4f1d62ec7d924168820c60bf37f592c4
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05712403

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