Isovanillin → 5-Hydroxy-1-indanone

HRID 2039805ノート

反応式

HRID 2039805 の反応式
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

参加物

3

反応物 2

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

生成物 1

HCID 2331475-Hydroxy-1-indanone

実験手順

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.

出典と根拠

ORDレコード
ord-1713125cf6cc4d2f928d9fda84d46411
出典データセット
uspto-grants-2013_11
特許番号
US08580822B2

反応ノート

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