2'-Hydroxy-4',6'-bis(methoxymethoxy)-3'-(3-methyl2-butenyl)acetophenone → 2'-Hydroxy-3'-isopentyl-4',6'-bis(methoxymethoxy)acetophenone
Reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])=[C:6]([O:13][CH2:14][O:15][CH3:16])[CH:5]=[C:4]([O:17][CH2:18][O:19][CH3:20])[C:3]=1[C:21](=[O:23])[CH3:22].[H][H]>C(O)C>[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[C:6]([O:13][CH2:14][O:15][CH3:16])[CH:5]=[C:4]([O:17][CH2:18][O:19][CH3:20])[C:3]=1[C:21](=[O:23])[CH3:22]Participants
Procedure
A solution of 2.08 g of the 2'-hydroxy-4',6'-bis(methoxymethoxy)-3'-(3-methyl-2-butenyl)acetophenone obtained in Production Example 13 in ethanol (20 ml) was added to a sufficiently hydrogen gas-absorbed suspension of 1.0 g of 5% palladium-carbon in 30 ml of ethanol, and the mixture was stirred at room temperature under atmospheric pressure in a hydrogen atmosphere. After the reaction, the reaction mixture was filtered, and the solvent was removed from the filtrate by distillation. The obtained residue was subjected to the silica gel column chromatography (3.0 cm in diameter, 60 g of silica gel, 0.3 kg/cm2) using a mixed solvent of n-hexane and ethyl acetate (n-hexane/ethyl acetate-3/1). Fractions of 50 ml were recovered, and 1.73 g (yield=82.8%) of 2'-hydroxy-3'-isopentyl-4',6'-bis(methoxymethoxy)acetophenone in the form of a yellow oil was obtained from the third to fifth fractions.
Workup
- customgas-absorbed
- additionsuspension of 1.0 g of 5% palladium-carbon in 30 ml of ethanol
- customAfter the reaction
- filtrationthe reaction mixture was filtered
- customthe solvent was removed from the filtrate by distillation
- customFractions of 50 ml were recovered
Sources & evidence
- ORD record
- ord-947296a762f14e6da0e7590ae1fa0b2e
- Source dataset
- uspto-grants-1992_04
- Patent number
- US05106871
Reaction notes
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