Butyryl chloride → HCID 13824273, compound
Reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[CH2:6][CH:7]([C:9]([O:11]CC)=[O:10])[O:8][C:4]=2[C:3]=1[Cl:16].[C:17](Cl)(=[O:21])[CH2:18][CH2:19][CH3:20].[Cl-].[Al+3].[Cl-].[Cl-]>>[C:17]([C:15]1[C:2]([Cl:1])=[C:3]([Cl:16])[C:4]2[O:8][CH:7]([C:9]([OH:11])=[O:10])[CH2:6][C:5]=2[CH:14]=1)(=[O:21])[CH2:18][CH2:19][CH3:20]Participants
Conditions
- Temperature
- 25 °C
Procedure
To a stirred solution of ethyl 6,7-dichloro-2,3-dihydro-2-benzofurancarboxylate (13.4 g, 0.05 mole) and butyryl chloride (10 ml, 0.09 mole) in CH2Cl 2 (30 ml) cooled to 5° C. in an ice bath was added aluminum chloride (22.5 g, 0.17 mole) over a 10 minute period. The reaction mixture was stirred for 1 hour at 25° C. then for 20 minutes at reflux. The reaction mixture was poured into ice water, extracted into ether, washed with water and the ether evaporated in vacuo. The residue was treated with 10 N sodium hydroxide (100 ml) and the resultant sodium salt filtered and suspended in dilute hydrochloric acid which was extracted with ether (206 ml), washed with water, dried over magnesium sulfate, evaporated to 50 ml and treated with hexane to give 12.0 g of 5-butyryl-6,7-dichloro-2,3-dihydro-2-benzofurancarboxylic acid which melted at 124°-125° C.
Workup
- temperaturefor 20 minutes at reflux
- extractionextracted into ether
- washwashed with water
- customthe ether evaporated in vacuo
- additionThe residue was treated with 10 N sodium hydroxide (100 ml)
- filtrationthe resultant sodium salt filtered
- extractionwas extracted with ether (206 ml)
- washwashed with water
- dry with materialdried over magnesium sulfate
- customevaporated to 50 ml
- additiontreated with hexane
Sources & evidence
- ORD record
- ord-b84c3414d91b43e7a6932ea3fd0bab87
- Source dataset
- uspto-grants-1987_03
- Patent number
- US04654365
Reaction notes
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