Hydrochloric Acid → Idebenone acid

HRID 1390567ノート

反応式

HRID 1390567 の反応式
N(S([O-])(=O)=O)(S([O-])(=O)=[O:4])[O].[K+].[K+].[OH:13][C:14]1[C:19]([O:20][CH3:21])=[C:18]([O:22][CH3:23])[CH:17]=[C:16]([CH3:24])[C:15]=1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([OH:36])=[O:35].Cl>O.[OH-].[Na+].CC(C)=O>[CH3:21][O:20][C:19]1[C:14](=[O:13])[C:15]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([OH:36])=[O:35])=[C:16]([CH3:24])[C:17](=[O:4])[C:18]=1[O:22][CH3:23]

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 3032624Potassium nitrosodisulfonateHCID 1290613810-(2-Hydroxy-3,4-dimethoxy-6-methylphenyl)decanoic acid

生成物 1

HCID 10020898Idebenone acid

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

A solution of potassium nitrosodisulfonate (0.8 part) in water (10 volume parts) was added to a solution of 10-(2'-hydroxy-3',4'-dimethoxy-6'-methylphenyl)decanoic acid (formula II-2 wherein R=H3CO, X=H, Y=OH, n=8, in the free form) (0.097 part) in a mixture of 1% sodium hydroxide (0.67 volume part) and acetone (2 volume parts) and the mixture was stirred at room temperature for 2 hours. The reaction mixture was rendered acidic with dilute hydrochloric acid and extracted with diethyl ether. The extract was washed with water and dried, followed by evaporation to dryness. The procedure provided 2,3-dimethoxy-5-methyl-6-(9'-carboxynonyl)-1,4-benzoquinone (formula I-2 wherein R=H3CO, n=8, in the free form) (0.099 part) as orange-colored needles melting at 59°-60.5° C.

後処理

  1. extractionextracted with diethyl ether
  2. washThe extract was washed with water
  3. customdried
  4. customfollowed by evaporation to dryness

出典と根拠

ORDレコード
ord-b83d2165c8e842a695448bb2a719e66e
出典データセット
uspto-grants-1979_02
特許番号
US04139545

反応ノート

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