Hydrogen Cyanide → Carvone, (+-)-

HRID 2044213노트

반응식

HRID 2044213 반응식
[CH3:1][C:2]1[C:7](=[O:8])[CH2:6][C@H:5]([C:9]([CH3:11])=[CH2:10])[CH2:4][CH:3]=1.C(C1CC(=O)C(C)=CC1)=CC(=C)C.C[O-].[Na+].O.[H][H].C#N>>[CH3:1][C:2]1[C:7](=[O:8])[CH2:6][CH:5]([C:9]([CH3:11])=[CH2:10])[CH2:4][CH:3]=1

참가 물질

7

반응물 6

HCID 768Hydrogen Cyanide2회HCID 962WaterHCID 439570Carvone, (-)-2회HCID 10942334Sodium MethoxideHCID 866538335-Isoprenyl-2-methylcyclohex-2-enoneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 7439Carvone, (+-)-

실험 절차

1379.4 g (9 mol) of R-(−)-carvone (5-isoprenyl-2-methylcyclohex-2-enone) with a purity of 98% (5-isoprenyl-2-methylcyclohex-2-enone) were heated in a 4000 ml glass flask to approx. 150° C. with stirring. At 144° C., 18.4 g of 30% sodium methoxide in water (0.1 mol) were added and then a mixture of 1287.9 g (8.4 mol) of 98% R-(−)-carvone (5-isoprenyl-2-methylcyclohex-2-enone) and 330.5 g (12.15 mol) of hydrogen cyamide (HCN) was added dropwise at 136-148° C. with stirring within 8 h. The postreaction time was approx. one hour. Subsequently, the HCN conversion was checked, and was 99.5%. The entire raw output weighed 3014 g and had a dark red color. The raw output was distilled through a Vigreux column. The first fraction recovered was unconverted carvone (approx. 900 g), and, after a mixed fraction (147.5 g), 1809.8 g of carvonenitrile were obtained with a purity of 98-99% (gas chromatography).

후처리

  1. additionwas added dropwise at 136-148° C.
  2. stirringwith stirring within 8 h
  3. distillationThe raw output was distilled through a Vigreux column
  4. customThe first fraction recovered
  5. customafter a mixed fraction (147.5 g), 1809.8 g of carvonenitrile were obtained with a purity of 98-99% (gas chromatography)

출처 및 근거

ORD 기록
ord-64557c6b8cad4b14b7e94d60fd59ccfa
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586794B2

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