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

HRID 31211

反応式

HRID 31211 の反応式
[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

参加物

6

反応物 5

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

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2fcfd03fce7d4ecc89399f53249338e3
出典データセット
uspto-grants-2008_09
特許番号
US07425568B2

関連ノート

読み込み中…