Phenol → 10-(4-Hydroxy-phenyl)-10-oxo-decanoic acid

HRID 2390592

반응식

HRID 2390592 반응식
[O:1]1[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=[O:13].[C:14]1([OH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[Cl-].[Cl-].[Al+3]>C(=S)=S>[OH:20][C:14]1[CH:19]=[CH:18][C:17]([C:2](=[O:13])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:1])=[O:12])=[CH:16][CH:15]=1

참가 물질

5

반응물 3

HCID 996PhenolHCID 75712Oxacycloundecane-2,11-dioneHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 1155086610-(4-Hydroxy-phenyl)-10-oxo-decanoic acid

시약·촉매·용매 1

HCID 6348Carbon Disulfide용매

실험 절차

To a 500 mL flask, equipped with mechanical stirrer and under inert atmosphere, was added Oxacycloundecane-2,11-dione (20 g, 108.5 mmol), phenol (10.22 g, 108.5 mmol), and 200 mL carbon disulfide. Aluminum (III) trichloride (72.34 g, 542 mmol) was added and the reaction was stirred for 72 hours. Carbon disulfide was decanted away, and ice was carefully added until most of mixture was dissolved. The insoluble material was collect by suction filtration and washed with 2×100 mL of water. The solid was then dissolved in 100 mL of 1 M aqueous sodium hydroxide and then carefully acidified with 1 M aqueous hydrochloric acid until pH=7.5 The solids that formed were removed by filtration and the parent solution was continued to be acidified until pH 2.5. The crude product precipitate was collected by filtration and was washed with 1×100 mL water. The crude product was dissolved in 100 mL of 1 M aqueous sodium hydroxide and then carefully acidified with 1 M aqueous hydrochloric acid until pH=7.5 and the impurities that precipitated were filtered off. The parent solution was further acidified until pH 2. The crude product was collected by filtration and washed with 2×50 mL water. The product was recrystallized form acetone. The isolated product (1.2 g, 4%) was collected by filtration. Found: C, 69.00; H, 7.81%; C16H22O4 requires C, 69.04; H, 7.97%; 1H NMR (d6-DMSO): δ 12.0, bs, 1H (COOH); δ 10.3, bs, 1H (aryl-hydroxyl); δ 7.8 d, 2H (aryl H's); δ 6.8, d, 2H, (aryl H's); δ 2.9, t, 2H (CH2 α to carbonyl); δ 2.2, t, 2H (CH2 α to COOH); δ 1.5, multiplet, 4H (CH2's β to carbonyl & β to COOH), δ 1.3, multiplet, 8H (rest of CH2's).

후처리

  1. customTo a 500 mL flask, equipped with mechanical stirrer and under inert atmosphere
  2. customCarbon disulfide was decanted away
  3. additionice was carefully added until most of mixture
  4. dissolutionwas dissolved
  5. filtrationThe insoluble material was collect by suction filtration
  6. washwashed with 2×100 mL of water
  7. dissolutionThe solid was then dissolved in 100 mL of 1 M aqueous sodium hydroxide
  8. customthat formed
  9. customwere removed by filtration
  10. filtrationThe crude product precipitate was collected by filtration
  11. washwas washed with 1×100 mL water
  12. dissolutionThe crude product was dissolved in 100 mL of 1 M aqueous sodium hydroxide
  13. customthe impurities that precipitated
  14. filtrationwere filtered off
  15. filtrationThe crude product was collected by filtration
  16. washwashed with 2×50 mL water
  17. customThe product was recrystallized form acetone
  18. filtrationThe isolated product (1.2 g, 4%) was collected by filtration

출처 및 근거

ORD 기록
ord-2a06fbfba3ed4a2391883fbcaca50132
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273794B2

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