Potassium Carbonate → Methyl 2-(2-propenyl-phenyloxy)propionate

HRID 1295459ノート

反応式

HRID 1295459 の反応式
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])=[CH:2][CH3:3].C1(OCC=C)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:28]([CH3:33])[C:29]([O:31][CH3:32])=[O:30]>O.CN(C)C=O>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH:28]([CH3:33])[C:29]([O:31][CH3:32])=[O:30])=[CH:2][CH3:3]

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 74458Allyl phenyl etherHCID 930292-PropenylphenolHCID 95576Methyl 2-bromopropionate

生成物 1

HCID 69460067Methyl 2-(2-propenyl-phenyloxy)propionate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 500 mg (3.72 mmol) of 2-propenylphenol (E/Z mixture), prepared by Claisen rearrangement of phenylallylether followed by double bond isomerisation, 1.02 g of potassium carbonate (0.74 mmol) and 745 mg of rac. methyl 2-bromopropionate (4.46 mmol) and 10 ml of dimethylformamide was stirred overnight at RT and then for 4 hours at 80° C. The reaction mixture was then added to 40 ml of water and extracted three times with 30 ml diethyl ether. The organic phase was washed with 5% sodium hydroxide solution, separated off, dried with Na2SO4 and concentrated by evaporation. 685 mg (83.6% of theory) of virtually pure methyl 2-(2-propenyl-phenyloxy)propionate were obtained.

後処理

  1. waitfor 4 hours at 80° C
  2. extractionextracted three times with 30 ml diethyl ether
  3. washThe organic phase was washed with 5% sodium hydroxide solution
  4. customseparated off
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-a3d320e3924f415a8cea6b4dcf6026b9
出典データセット
uspto-grants-2007_07
特許番号
US07241898B2

反応ノート

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