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

HRID 234206

반응식

HRID 234206 반응식
[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]

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 664601,1,3,3-TetramethylguanidineHCID 11160120HCID 11160120, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 42.0 g of (RS)-3,4-dihydroxy-6-methoxy-7-methyl-1,3-dihydro-isobenzofuran-1-one in 11 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.

후처리

  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

출처 및 근거

ORD 기록
ord-35165ccd92074d9f882603017b1eb95a
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05594135

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