Hydrochloric Acid → 3-(Methoxycarbonyl)-4-methylbenzoic acid
Reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([CH3:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])=[O:2].[OH:14]OS([O-])=O.[K+].O.Cl>CN(C=O)C.CCOC(C)=O>[CH3:11][O:10][C:8]([C:7]1[CH:12]=[C:3]([CH:4]=[CH:5][C:6]=1[CH3:13])[C:1]([OH:14])=[O:2])=[O:9]Participants
7
Procedure
A mixture of 268 mg of the methyl 5-formyl-2-methylbenzoate and 1.08 g (1.76 mmol) of Oxone in 6 mL of DMF was stirred at r.t. for 16.75 h. Water, 1N HCl, and EtOAc were added, and the aqueous layer was extracted with EtOAc. The combined extracts were dried over Na2SO4, filtered, and concentrated, and 3-(methoxycarbonyl)-4-methylbenzoic acid, which was used for the next reaction without further purification.
Workup
- extractionthe aqueous layer was extracted with EtOAc
- dry with materialThe combined extracts were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- custom3-(methoxycarbonyl)-4-methylbenzoic acid, which was used for the next reaction without further purification
Sources & evidence
- ORD record
- ord-430dedf4208244fc83ed6b0850c8dd3a
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299267B2
Reaction notes
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