Methyl Ethyl Ketone → 1-(2,5-Bis(benzyloxy)phenyl)ethanone

HRID 31211

반응식

HRID 31211 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:20](=O)([O-])[O-].[K+].[K+].C1O[CH2:42][CH2:41]OCCOCCOCCOCCOC1.[CH3:44][C:45](=O)[CH2:46][CH3:47]>>[CH2:12]([O:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:20][C:42]2[CH:41]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

6

반응물 5

HCID 6569Methyl Ethyl KetoneHCID 7503Benzyl ChlorideHCID 102792-AcetylhydroquinoneHCID 11430Potassium CarbonateHCID 2855718-Crown-6

생성물 1

HCID 127460231-(2,5-Bis(benzyloxy)phenyl)ethanone

실험 절차

A mixture of 1-(2,5-dihydroxyphenyl)ethanone (3.16 g), benzyl chloride (7.04 g), potassium carbonate (12.4 g) and 18-Crown-6 (30 mg) in 2-butanone (50 ml) was heated under reflux for 5 hrs. After cooling the precipitate was filtered off. The filtrate was evaporated to dryness under reduced pressure and ether (50 ml) was added to it. The solution was washed twice with dilute sodium hydroxide solution, twice with dilute hydrochloric acid, dried over sodium sulphate and substantially evaporated to dryness under reduced pressure. The residue was triturated with cold n-heptane (30 ml), and the precipitate was filtered off with suction filtration giving after drying 2.85 g of 1-[2,5-Bis(benzyloxy)phenyl]ethanone. 1H NMR (400 MHz, DMSO-d6) δ=2.50 (s, 3H), 5.08 (s, 2H), 5.18 (s, 2H), 7.20-7.50 (m, 13H).

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hrs
  3. temperatureAfter cooling the precipitate
  4. filtrationwas filtered off
  5. customThe filtrate was evaporated to dryness under reduced pressure and ether (50 ml)
  6. additionwas added to it
  7. washThe solution was washed twice with dilute sodium hydroxide solution, twice with dilute hydrochloric acid
  8. dry with materialdried over sodium sulphate
  9. customsubstantially evaporated to dryness under reduced pressure
  10. customThe residue was triturated with cold n-heptane (30 ml)
  11. filtrationthe precipitate was filtered off with suction filtration
  12. customgiving
  13. dry with materialafter drying 2.85 g of 1-[2,5-Bis(benzyloxy)phenyl]ethanone

출처 및 근거

ORD 기록
ord-2fcfd03fce7d4ecc89399f53249338e3
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425568B2

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