Hydrogen Bromide → HCID 20281919, compound
Reaction equation
[CH3:1][CH:2]1[CH2:9][CH2:8][CH2:7][CH2:6][O:5][C:3]1=[O:4].[BrH:10].S(=O)(=O)(O)O>O>[Br:10][CH2:6][CH2:7][CH2:8][CH2:9][CH:2]([CH3:1])[C:3]([OH:5])=[O:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
To 2-methylcaprolactone (1.8 g, 14 mmole) was added a solution mixture of 47% aqueous hydrobromic acid (10.5 ml) and concentrated sulfuric acid (2.6 ml), and the reaction was conducted under heating at 130° C. for 3 hours. After the reaction solution was cooled, water was added, and the product was extracted with ether. The organic layer was washed with water, dried and the solvent was evaporated in vacuo. The residue was chromatographed on a column of silica gel using isopropyl ether to give 6-bromo-2-methylhexanoic acid (1.56 g, 53.3%) [NMR (δ value): 1.18 (3H,d,6 Hz), 2.25-2.8 (1H,m), 3.40 (2H,t,6 Hz), 11.56 (1H,COOH)].
Workup
- temperatureAfter the reaction solution was cooled
- extractionthe product was extracted with ether
- washThe organic layer was washed with water
- customdried
- customthe solvent was evaporated in vacuo
- customThe residue was chromatographed on a column of silica gel
Sources & evidence
- ORD record
- ord-b1ba698891924dc48c2803929127562a
- Source dataset
- uspto-grants-1985_05
- Patent number
- US04518602
Reaction notes
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