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

HRID 1969896노트

반응식

HRID 1969896 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-14ee3734f31949289f06eae7c604274f
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426411B2

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