1,2-Dimethoxyethane → HCID 21487614, 화합물

HRID 1414482

반응식

HRID 1414482 반응식
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6](O)=[CH:5][CH:4]=1)[CH3:2].[CH2:10]([CH2:13][O:14][CH3:15])OC.[OH-].[K+].BrC[CH2:20][CH:21]([CH3:28])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26]>C(O)C.CCCCCC>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:15]([O:14][CH:13]([C:6]2[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=2)[CH2:10][CH:25]([CH3:26])[CH2:24][CH2:23][CH:22]=[C:21]([CH3:28])[CH3:20])[CH2:28][CH:21]([CH3:20])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:26])[CH3:27])=[CH:5][CH:4]=1)[CH3:2]

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 14797Potassium HydroxideHCID 312424-EthylphenolHCID 43282458-Bromo-2,6-dimethyloct-2-ene

생성물 1

HCID 21487614HCID 21487614, 화합물

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8058Hexane용매

실험 절차

Into a 2 liter round-bottomed flask equipped with a cooling bath, stirrer and thermometer was placed 70 g. of p-ethylphenol and 400 ml dimethoxy ethane. The resulting solution was stirred and 30 g. of potassium hydroxide in 200 ml ethanol was added within 5 minutes. The temperature was maintained below 20° C during this addition and then 110 g. of 1-bromo-3,7-dimethyl-6-octene was added dropwise over 15 minutes. The reaction was stirred for two hours longer at 80° C and then allowed to rise to room temperature. After 3 hours the reaction was poured into a mixture of 500 g. of ice and 1 liter of hexane. The phases were separated and the aqueous layer was reextracted with two 0.5 l-portions hexane. All organic phases were combined and washed successively with 1.0 liter of water, two 250 ml portions of 2N sodium hydroxide and 1.0 liter of water. The organic layer was then dried over sodium sulfate, filtered, and concentrated in vacuo with water aspirator. The dark solution was chromatographed on 1 kg silica gel in hexane-ethylacetate (9:1 parts by volume). The fractions yielding p-ethyphenyl-3,7-dimethyl-6-octenyl ether were concentrated in a rotary evaporator at 40° C bath temperature using a water pump for the vacuum. The residue was distilled through a small Widmer column. The fraction of b.p. 118°-120° C 0.05 mmHg was p-ethylphenyl-3,7-dimethyl-6-octenyl ether.

후처리

  1. customInto a 2 liter round-bottomed flask equipped with a cooling bath, stirrer
  2. temperatureThe temperature was maintained below 20° C during this addition
  3. stirringThe reaction was stirred for two hours longer at 80° C
  4. customto rise to room temperature
  5. additionAfter 3 hours the reaction was poured into a mixture of 500 g
  6. customThe phases were separated
  7. washwashed successively with 1.0 liter of water, two 250 ml portions of 2N sodium hydroxide and 1.0 liter of water
  8. dry with materialThe organic layer was then dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo with water aspirator
  11. customThe dark solution was chromatographed on 1 kg silica gel in hexane-ethylacetate (9:1 parts by volume)

출처 및 근거

ORD 기록
ord-4ec25ae1bd184c92ab7b1246274b39ee
출처 데이터셋
uspto-grants-1977_01
특허 번호
US04001339

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