M-Cresol → 2-(3-Methylphenoxy)ethyl acetate

HRID 1679339ノート

反応式

HRID 1679339 の反応式
[O-]CC.[Na+].[Na].[CH:6]1[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(O)C>[C:16]([O:18][CH2:19][CH2:20][O:12][C:11]1[CH:6]=[C:7]([CH3:13])[CH:8]=[CH:9][CH:10]=1)(=[O:17])[CH3:15]

参加物

6

反応物 4

HCID 342M-CresolHCID 7748Ethyl bromoacetateHCID 2723922Sodium ethoxideHCID 5360545Sodium

生成物 1

HCID 3030952-(3-Methylphenoxy)ethyl acetate収率 59.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of sodium ethoxide prepared from 25 g (1.1 mol) sodium metal in 800 ml ethanol was added 108 g (1.0 mol) m-cresol. After warming at reflux for 1.5 hr, 167 g (1.0 mol) ethyl bromoacetate was added dropwise as reflux continued. After 5.5 hr reflux, the reaction mixture was cooled and NaBr removed by filtration. The filtrate was concentrated to 200 ml volume and extracted with 3 × 300 ml ether. The combined ether layers were washed with pH 10.5 NaOH solution, saturated NaCl solution and were dried over anhydrous MgSO4. The ether was removed under reduced pressure and the residual yellow oil distilled at 105°/1 mm Hg to give 115.3 g m-tolyloxyethyl acetate.

後処理

  1. temperatureAfter warming
  2. temperatureat reflux for 1.5 hr
  3. temperatureas reflux
  4. temperatureAfter 5.5 hr reflux
  5. temperaturethe reaction mixture was cooled
  6. customNaBr removed by filtration
  7. concentrationThe filtrate was concentrated to 200 ml volume
  8. extractionextracted with 3 × 300 ml ether
  9. washThe combined ether layers were washed with pH 10.5 NaOH solution, saturated NaCl solution
  10. dry with materialwere dried over anhydrous MgSO4
  11. customThe ether was removed under reduced pressure
  12. distillationthe residual yellow oil distilled at 105°/1 mm Hg

出典と根拠

ORDレコード
ord-fa1e9772f7104428ad00978aa69dec9f
出典データセット
uspto-grants-1978_03
特許番号
US04080454

反応ノート

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