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Acetaldehyde → 3-Hydroxy-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-1-one

HRID 1680106
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HRID 1680106 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1[C:10](=[O:12])[CH3:11].C.[CH:14](=[O:16])[CH3:15]>C(O)(=O)C>[OH:16][CH:14]([CH3:15])[CH2:11][C:10]([C:3]1[C:4]([CH3:8])([CH3:9])[CH2:5][CH:6]=[CH:7][C:2]=1[CH3:1])=[O:12]
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참가 물질

5

반응물 3

HCID 177Acetaldehyde2회HCID 297MethaneHCID 6451733Ethanone, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-

생성물 1

HCID 156245463-Hydroxy-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-1-one

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

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온도
10 °C

실험 절차

Into a 1-liter reaction flask equipped with a mechanical stirrer, cooling bath, 250 ml addition funnel, nitrogen purge, water-cooled condenser, gas bubbler and thermometer, is placed 427 ml (1.3 moles) of a 3-molar solution of methyl magnesium chloride in tetrahydrofuran. 200 Grams (1.22 moles) of 2,6,6-trimethyl-1-acetylcyclohexa-1,3-diene are added dropwise from the addition funnel at a rate sufficient to produce methane. Cooling is applied as necessary to maintain the reaction temperature between 30° and 35° C. Following completion of the addition of the 2,6,6-trimethyl-1-acetylcyclohexa-1,3-diene, the reaction mass is stirred until no further methane is evolved. The reaction mass is then cooled to a temperature in the range of from 0° C. to 5° C., and 59 grams of acetaldehyde is added dropwise with stirring while maintaining the reaction mass temperature at about 10° C. The reaction is slightly exothermic. 15 Minutes after the completion of the addition of acetaldehyde, acetic acid is added dropwise while maintaining the temperature of the reaction mass at about 10° C. Following the addition of acetic acid, the reaction mass is permitted to reach room temperature. The reaction mass is then washed into a separatory funnel with water to dissolve the salt therein. The resulting organic layer is washed with saturated sodium chloride, saturated sodium bicarbonate, and then saturated sodium chloride. The washed organic layer is then dried over anhydrous magnesium sulfate and concentrated on a rotovap yielding 256 grams of residue.

후처리

  1. temperatureCooling
  2. temperatureto maintain the reaction temperature between 30° and 35° C
  3. additionis added dropwise
  4. additionis added dropwise
  5. temperaturewhile maintaining the temperature of the reaction mass at about 10° C
  6. customto reach room temperature
  7. washThe reaction mass is then washed into a separatory funnel with water
  8. dissolutionto dissolve the salt
  9. washThe resulting organic layer is washed with saturated sodium chloride, saturated sodium bicarbonate
  10. dry with materialThe washed organic layer is then dried over anhydrous magnesium sulfate
  11. concentrationconcentrated on a rotovap

출처 및 근거

ORD 기록
ord-98fd949423d24f7eb00817c4684ac3b0
출처 데이터셋
uspto-grants-1981_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04271853

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