Isovanillin → 5-Hydroxy-1-indanone

HRID 2039805Notes

Reaction equation

HRID 2039805 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-1713125cf6cc4d2f928d9fda84d46411
Source dataset
uspto-grants-2013_11
Patent number
US08580822B2

Reaction notes

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