Isovanillin → 5-Hydroxy-1-indanone

HRID 888047

Reaction equation

HRID 888047 reaction equation
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

Participants

3

Reactant 2

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

Product 1

HCID 2331475-Hydroxy-1-indanone

Procedure

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.

Sources & evidence

ORD record
ord-fdc6aab35c544b66941c64fa13c8cb40
Source dataset
uspto-grants-2012_08
Patent number
US08247563B2

Linked notes

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