Hydrochloric Acid → Methyl 2-hydroxy-1-methoxy-5-methyl-4-oxocyclohex-2-enecarboxylate

HRID 1861601

反応式

HRID 1861601 の反応式
C[O-].[Na+].[CH3:4][C:5](=[CH2:9])[C:6](=[O:8])[CH3:7].[CH3:10][O:11][CH:12]([C:17]([O:19]C)=O)[C:13]([O:15][CH3:16])=[O:14].Cl>CS(C)=O>[OH:19][C:17]1[C:12]([O:11][CH3:10])([C:13]([O:15][CH3:16])=[O:14])[CH2:4][CH:5]([CH3:9])[C:6](=[O:8])[CH:7]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 13143Methyl isopropenyl ketoneHCID 78718Dimethyl methoxymalonateHCID 10942334Sodium Methoxide

生成物 1

HCID 18755506Methyl 2-hydroxy-1-methoxy-5-methyl-4-oxocyclohex-2-enecarboxylate

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
35 °C

実験手順

A 30% solution of 35.8 g of sodium methoxide is introduced into 65 ml of dimethyl sulfoxide and, within 20 minutes, treated with a mixture of 16.7 g of 3-methyl-3-butene-2-one and 32.4 g of dimethyl methoxymalonate at a temperature of 30-35° C. The mixture is stirred for 1 hour at a temperature of 35° C., and is then acidified with hydrochloric acid and extracted repeatedly with dichloromethane. The organic phases are washed with water, dried and concentrated. Crystallization from hot ethyl acetate and hexane gives pure methyl 2-hydroxy-1-methoxy-5-methyl-4-oxocyclohex-2-enecarboxylate of melting point 117-117.5° C.

後処理

  1. extractionextracted repeatedly with dichloromethane
  2. washThe organic phases are washed with water
  3. customdried
  4. concentrationconcentrated
  5. customCrystallization from hot ethyl acetate and hexane

出典と根拠

ORDレコード
ord-24320ccc67c04b4f96aadf7909846525
出典データセット
uspto-grants-2003_03
特許番号
US06534445B1

関連ノート

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