Isovanillin → 5-Hydroxy-1-indanone

HRID 888047

반응식

HRID 888047 반응식
O[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][C:3]=1[O:12]C.COC1C=CC(C=O)=CC=1O>>[OH:12][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:2]=1)[C:8](=[O:11])[CH2:7][CH2:6]2

참가 물질

3

반응물 2

HCID 12127IsovanillinHCID 2331486-hydroxy-5-methoxy-2,3-dihydro-1H-inden-1-one

생성물 1

HCID 2331475-Hydroxy-1-indanone

실험 절차

The indanone building blocks (18) were prepared as described in Scheme 11. The commercially available vanillin (33a) was reacted with Wittig reagent (34) in toluene at reflux temperature to give the corresponding unsaturated ester (35a) as cis and trans mixture. The ester (35a) was subjected to hydrogenation using palladium-carbon catalyst in methanol to give the saturated ester (36a). The ester (36a) was hydrolyzed using aqueous potassium hydroxide in THF to give carboxylic acid which after cyclization in the presence of concentrated sulfuric acid gave the target 6-hydroxyindan-1-one (18a) in overall good yield. Similarly, 5-hydroxyindan-1-one (18b) was prepared from the commercially available starting building block isovanilin (33b) in overall good yields.

출처 및 근거

ORD 기록
ord-fdc6aab35c544b66941c64fa13c8cb40
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247563B2

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