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Hydrochloric Acid → 3-(Hydroxymethyl)-4-methylpent-4-en-2-one

HRID 1834160
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HRID 1834160 반응식
[CH2:1]=[O:2].[O:3]=[C:4]([CH:6]=[C:7]([CH3:9])[CH3:8])[CH3:5].N12CCCN=C1CCCCC2.Cl>>[CH3:8][C:7]([CH:6]([CH2:1][OH:2])[C:4](=[O:3])[CH3:5])=[CH2:9]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 4

HCID 313Hydrochloric AcidHCID 712Formaldehyde2회HCID 8858Mesityl oxideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

생성물 1

HCID 141866443-(Hydroxymethyl)-4-methylpent-4-en-2-one수율 78%

실험 절차

30 g (1 mol) of paraformaldehyde were added to a mixture of 490 g (5 mols) of mesityl oxide and 15.2 g (0.1 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene over the course of 2 - 3 hours at 30° C. After completion of the addition of formaldehyde, the reaction mixture was stirred for about a further hour, then cooled to 0° C and neutralised with dilute hydrochloric acid. The organic phase was separated off and the aqueous phase was repeatedly extracted with methylene chloride. The combined organic phases were dried with zeolite, filtered off and then freed from methylene chloride. The residue (506 g) was fractionally distilled in a high vacuum at about 0.1 - 1 mm Hg. Thereby, 431 g of mesityl oxide were recovered. As a further fraction, 47 g of crude product of boiling point 45° - 85° C/l mm Hg were obtained. A further fractional distillation of this crude product gave 35.5 g of 2-methyl-3-hydroxymethyl-pent-1-en-4-one of boiling point 50° - 52° C/0.2 mm Hg (yield: 78%, relative to mesityl oxide converted), in the form of a colourless liquid.

후처리

  1. customThe organic phase was separated off
  2. extractionthe aqueous phase was repeatedly extracted with methylene chloride
  3. dry with materialThe combined organic phases were dried with zeolite
  4. filtrationfiltered off
  5. distillationThe residue (506 g) was fractionally distilled in a high vacuum at about 0.1 - 1 mm Hg
  6. customThereby, 431 g of mesityl oxide were recovered
  7. customAs a further fraction, 47 g of crude product of boiling point 45° - 85° C/l mm Hg were obtained
  8. distillationA further fractional distillation of this crude product

출처 및 근거

ORD 기록
ord-4967a8562db248d68fb817a1c41fd378
출처 데이터셋
uspto-grants-1978_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04069257

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