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Dimethyl Sulfate → 4-(2',5'-Dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenol

HRID 1789598
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HRID 1789598 반응식
[OH:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[C:5](O)=[C:4]([CH3:11])[C:3]=1[CH2:12][CH:13]=[C:14]([CH3:17])CO.[OH-].[Na+].[C:20](=[O:23])([O-])[O-].[K+].[K+].S([O:31][CH3:32])(OC)(=O)=O.[Br-].[C:34]([NH3+])(C)(C)C>O.C(Cl)Cl>[CH3:34][O:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[C:5]([O:31][CH3:32])=[C:4]([CH3:11])[C:3]=1[CH2:12][CH:13]=[C:14]([CH3:17])[CH2:20][OH:23]
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참가 물질

8

반응물 5

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 21584498Tert-butyl ammonium bromideHCID 543878904-(2',5'-Dihydroxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenol

생성물 1

HCID 542146164-(2',5'-Dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenol
수율 372.9%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6344Dichloromethane용매

반응 조건

온도
30 °C

실험 절차

A mixture of 3.0 g of 4-(2',5'-dihydroxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenol, 40 ml of methylene chloride, 6 ml of water, 5.6 g of sodium hydroxide, 0.6 g of potassium carbonate, 1.6 g of dimethyl sulphate and 0.25 g of tert.butylammonium bromide is stirred well at 30° C. under argon for 3 hours and thereafter poured into water. The aqueous mixture is extracted with diethyl ether, and the ether phase is washed in sequence with sodium bicarbonate solution and sodium chloride solution, dried over anhydrous sodium sulphate and evaporated to dryness. From the residue (3.7 g) there are obtained by column chromatography (silica gel, diethyl ether/n-hexane) 1.6 g of 4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenol in the form of white crystals, m.p. 87°-88° C.

후처리

  1. extractionThe aqueous mixture is extracted with diethyl ether
  2. washthe ether phase is washed in sequence with sodium bicarbonate solution and sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulphate
  4. customevaporated to dryness

출처 및 근거

ORD 기록
ord-6ee95f6e6ecf4cd4a00b3665941096fd
출처 데이터셋
uspto-grants-1987_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04689427

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