Chloroacetyl chloride → HCID 86682036, compound
Reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].Cl[CH2:6][C:7](Cl)=[O:8].[OH:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[C:12]=1[C:13]([OH:15])=[O:14].C(OCC)(=O)C>[N+](C1C=CC=CC=1)([O-])=O>[OH:10][C:11]1[CH:19]=[CH:18][C:17]2[C:7](=[O:8])[CH2:6][O:20][C:16]=2[C:12]=1[C:13]([OH:15])=[O:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A suspension of aluminum chloride (2.7 g, 21 mmol) in nitrobenzene (6.0 mL) was cooled to 0° C., and stirred. The suspension was added with chloroacetyl chloride (0.60 g, 6.2 mmol), and then added portionwise with a suspension of 2,6-dihydroxybenzoic acid (0.064 g, 4.1 mmol) in nitrobenzene (6.0 mL). After completion of the addition, the reaction mixture was stirred at 40° C. for 12 hours. The reaction mixture was added with ethyl acetate and ice water, the mixture was stirred at room temperature for 1 hour, and then the organic layer was separated. The organic layer was extracted with 2 N aqueous sodium hydroxide, and the aqueous layer was made acidic with 3 N hydrochloric acid. The precipitated solid was collected by filtration and dried to obtain 6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-carboxylic acid (0.76 g, 89%).
Workup
- additionAfter completion of the addition
- stirringthe reaction mixture was stirred at 40° C. for 12 hours
- stirringthe mixture was stirred at room temperature for 1 hour
- customthe organic layer was separated
- extractionThe organic layer was extracted with 2 N aqueous sodium hydroxide
- filtrationThe precipitated solid was collected by filtration
- customdried
Sources & evidence
- ORD record
- ord-b24305714cd34b248fcd37cefcb0f284
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156827B2
Reaction notes
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