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Acetic Anhydride → 3-(Tert-butyl)cyclopentanone

HRID 2096559
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HRID 2096559 반응식
[C:1]([CH:5]([CH2:10][CH2:11][CH2:12][OH:13])[CH2:6]C(O)=O)([CH3:4])([CH3:3])[CH3:2].CC([O-])=O.[Na+].C(OC(=O)C)(=O)C>C(O)(=O)C>[C:1]([CH:5]1[CH2:10][CH2:11][C:12](=[O:13])[CH2:6]1)([CH3:2])([CH3:3])[CH3:4]
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참가 물질

5

반응물 3

HCID 7918Acetic Anhydride2회HCID 517045Sodium AcetateHCID 86657444HCID 86657444, 화합물

생성물 1

HCID 3167693-(Tert-butyl)cyclopentanone수율 80.2%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A suspension of the 3-tert-butyl-6-hydroxyhexanoic acid (1 g, 4.95 mmol), anhydrous NaOAc (0.321 g, 3.91 mmol) and acetic anhydride was refluxed for 5 hours during which time the solution mixture turned black. After the reaction mixture was cooled to room temperature, the formed acetic acid and remaining acetic anhydride were removed on a rotary evaporator and then under high vacuum. The residue was then dissolved in ethyl acetate, filtered through a plug of celite to remove the precipitate NaOAc, and concentrated in vacuo to give the crude product of 3-tert-butylcyclopentanone (0.557 g, 58%).

후처리

  1. temperaturewas refluxed for 5 hours during which time the solution mixture
  2. customwere removed on a rotary evaporator
  3. dissolutionThe residue was then dissolved in ethyl acetate
  4. filtrationfiltered through a plug of celite
  5. customto remove the precipitate NaOAc
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-01823504858d41bc9523970b2efedafb
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08450308B2

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