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Formaldehyde → 6-Methyl-3-cyclohexene-1,1-dimethanol

HRID 1837420
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HRID 1837420 반응식
[CH3:1][CH:2]1[CH2:7][CH:6]=[CH:5][CH2:4][CH:3]1[CH:8]=[O:9].C=CC=C.[CH:14](=[O:18])/C=C/C.C=O.[OH-].[K+]>O.CO>[CH3:1][CH:2]1[C:3]([CH2:14][OH:18])([CH2:8][OH:9])[CH2:4][CH:5]=[CH:6][CH2:7]1
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참가 물질

8

반응물 5

HCID 712FormaldehydeHCID 78451,3-ButadieneHCID 14797Potassium HydroxideHCID 1015506-Methyl-3-cyclohexene-1-carboxaldehydeHCID 447466Crotonaldehyde

생성물 1

HCID 1389976-Methyl-3-cyclohexene-1,1-dimethanol수율 82%

시약·촉매·용매 2

HCID 887
Methanol
용매
HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

To a three-necked flask, 327 g of 2-methyl-4-cyclohexene-1-carboaldehyde, a Diels-Alder reaction product of butadiene and crotonaldehyde, 600 ml of methanol and 729 g of 37% of formalin were charged, and then the temperature of this solution was raised to 60° C. with stirring. Next, 252 g of KOH dissolved in 600 ml of distilled water was added dropwise thereto. After stirring for 7 hours, the reaction solution was concentrated under reduced pressure, which resulted in a residue with two phases. The oil phase concentrated to about 150 ml was washed with 300 ml of distilled water. After concentration under reduced pressure, 50 mg of 3,5-di(t-butyl)-4-hydroxytoluene (BHT) was added to the oil phase, and then vacuum distillation was carried out to yield 311 g (yield 82%) of 6-methyl-3-cyclohexene-1,1-dimethanol as a colorless crystal.

후처리

  1. additionwere charged
  2. additionwas added dropwise
  3. stirringAfter stirring for 7 hours
  4. concentrationthe reaction solution was concentrated under reduced pressure, which
  5. customresulted in a residue with two phases
  6. concentrationThe oil phase concentrated to about 150 ml
  7. washwas washed with 300 ml of distilled water
  8. concentrationAfter concentration under reduced pressure, 50 mg of 3,5-di(t-butyl)-4-hydroxytoluene (BHT)
  9. additionwas added to the oil phase
  10. distillationvacuum distillation

출처 및 근거

ORD 기록
ord-e38855075db9499d8eb7bccfe03858b1
출처 데이터셋
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06783840B2

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