Allyl bromide → 2-Formyl-3-hydroxy-5-methoxy-6-methylbenzoic acid allyl ester

HRID 1082146

反応式

HRID 1082146 の反応式
[OH:1][CH:2]1[C:10]2[C:5](=[C:6]([CH3:14])[C:7]([O:12][CH3:13])=[CH:8][C:9]=2[OH:11])[C:4](=[O:15])[O:3]1.CN(C)C(N(C)C)=N.[CH2:24](Br)[CH:25]=[CH2:26]>CN(C)C=O>[CH2:26]([O:3][C:4](=[O:15])[C:5]1[C:6]([CH3:14])=[C:7]([O:12][CH3:13])[CH:8]=[C:9]([OH:11])[C:10]=1[CH:2]=[O:1])[CH:25]=[CH2:24]

参加物

5

反応物 3

HCID 7841Allyl bromideHCID 664601,1,3,3-TetramethylguanidineHCID 11160120HCID 11160120、化合物

生成物 1

HCID 537352632-Formyl-3-hydroxy-5-methoxy-6-methylbenzoic acid allyl ester収率 74.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 42.0 g of (RS)-3,4-dihydroxy-6-methoxy-7-methyl-1,3-dihydro-isobenzofuran-1-one in 1 l of N,N-dimethylformamide were added 23.0 g of 1,1,3,3-tetramethylguanidine. The solution was stirred for 30 min and then, 48.4 g of allyl bromide were added and stirring was continued for 3 h. The mixture was evaporated in vacuo and the residue was dissolved in 0.7 l of ethyl acetate. The solution was washed with brine, dried over sodium sulfate, and the solvent was evaporated in vacuo. The solid residue was crystallized from tert-butyl methyl ether to give 37.3 g of 2-formyl-3-hydroxy-5-methoxy-6-methylbenzoic acid allyl ester as white crystals of m.p. 73°-74° C.

後処理

  1. stirringstirring
  2. waitwas continued for 3 h
  3. customThe mixture was evaporated in vacuo
  4. dissolutionthe residue was dissolved in 0.7 l of ethyl acetate
  5. washThe solution was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was evaporated in vacuo
  8. customThe solid residue was crystallized from tert-butyl methyl ether

出典と根拠

ORDレコード
ord-6277ae2d5df34dbf857f3a14457d4945
出典データセット
uspto-grants-1996_12
特許番号
US05589473

関連ノート

読み込み中…