Methanol → HCID 17909374, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[CH:10]([C:15]([O:17]C)=[O:16])[C:11]([O:13]C)=[O:12].CO.[OH-].[K+]>O>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[CH:10]([C:15]([OH:17])=[O:16])[C:11]([OH:13])=[O:12]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
10 g of dimethyl 2-chloro4,6-dimethylphenylmalonate according to Example (VI-1) were initially introduced and treated successively with 20 ml of methanol and 6.8 g of KOH dissolved in 9.1 ml of water. After an hour, the mixture was diluted with a further 20 ml of solvent (MeOH/water 1:1). The mixture was heated at reflux for 10 h, then cooled and concentrated. The residue which remained was taken up in a little water and washed once with toluene. The aqueous phase was then diluted further with water, added to the same amount of ether and cooled to about -10° C. It was acidified with concentrated HCl (pH 1), and the organic phase was separated off and reextracted a further 1 or 2 times. The combined organic phases were dried and concentrated. The residue was crystallized from toluene and afforded 7.6 g of 2-chloro-4,6-dimethylphenylmalonic acid having a melting point of 174 to 176° C. (decomposition).
Workup
- waitAfter an hour
- temperatureThe mixture was heated
- temperatureat reflux for 10 h
- temperaturecooled
- concentrationconcentrated
- washwashed once with toluene
- additionThe aqueous phase was then diluted further with water
- additionadded to the same amount of ether
- customthe organic phase was separated off
- customThe combined organic phases were dried
- concentrationconcentrated
- customThe residue was crystallized from toluene
Sources & evidence
- ORD record
- ord-98212e9848124591b2d14577cab6d158
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05994274
Reaction notes
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