Citric Acid → 8-Ethyl-1,4-dioxaspiro[4,4]nonane-7-carboxylic acid

HRID 1969896ノート

反応式

HRID 1969896 の反応式
[CH2:1]([CH:3]1[CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH:4]1[C:12]([O:14]CC)=[O:13])[CH3:2].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[CH2:1]([CH:3]1[CH2:11][C:6]2([O:7][CH2:8][CH2:9][O:10]2)[CH2:5][CH:4]1[C:12]([OH:14])=[O:13])[CH3:2]

参加物

5

反応物 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 58557462Ethyl 8-ethyl-1,4-dioxaspiro[4,4]nonane-7-carboxylate

生成物 1

HCID 585573038-Ethyl-1,4-dioxaspiro[4,4]nonane-7-carboxylic acid

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A round bottom flask was charged with ethyl 8-ethyl-1,4-dioxaspiro[4.4]nonane-7-carboxylate (0.32 g, 1.4 mmol) and aqueous sodium hydroxide (1 N, 14.0 mL, 14.0 mmol). The solution was stirred overnight at rt. To the solution was added DCM (30 mL) followed by the addition of 20% aqueous citric acid (about 20 mL) to reach pH of about 2. The layers were separated and the aqueous solution was extracted with DCM (2×30 mL) and DCM/EtOAc (1:1, 30 mL). The combined extracts were dried over anhydrous MgSO4, filtered, and concd under reduced pressure to give 8-ethyl-1,4-dioxaspiro[4.4]nonane-7-carboxylic acid as a clear, colorless oil (0.27 g, 96%): LC/MS (Table 1, Method c) Rt=1.20 min; MS m/z: 201 (M+H)+.

後処理

  1. customThe layers were separated
  2. extractionthe aqueous solution was extracted with DCM (2×30 mL) and DCM/EtOAc (1:1, 30 mL)
  3. dry with materialThe combined extracts were dried over anhydrous MgSO4
  4. filtrationfiltered

出典と根拠

ORDレコード
ord-14ee3734f31949289f06eae7c604274f
出典データセット
uspto-grants-2013_04
特許番号
US08426411B2

反応ノート

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