Hydrogen Bromide → HCID 19431593, compound

HRID 463049Notes

Reaction equation

HRID 463049 reaction equation
C(O[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10]([O:12]CC)=[O:11])(=O)C.[Cl-].[Na+].[BrH:23]>>[Br:23][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10]([OH:12])=[O:11]

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 5234Sodium ChlorideHCID 20281915HCID 20281915, compound

Product 1

HCID 19431593HCID 19431593, compoundYield 75%

Conditions

Temperature
130 °C

Procedure

Ethyl 6-acetoxy-2-phenylhexanoate (22 g) was dissolved in 47% aqueous hydrobromic acid (100 ml), and the solution was heated at 130° C. for 4 hours. After the completion of the reaction, the solution was cooled, and aqueous sodium chloride (300 ml) was added, followed by extraction of the product with isopropyl ether. The organic layer was washed with water, dried and concentrated under reduced pressure. The residue was chromatographed on a column of silica gel, and development was effected with isopropyl ether to give 6-bromo-2-phenylhexanoic acid (16 g, 75%).

Workup

  1. customAfter the completion of the reaction
  2. temperaturethe solution was cooled
  3. extractionfollowed by extraction of the product with isopropyl ether
  4. washThe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on a column of silica gel, and development

Sources & evidence

ORD record
ord-56b3bc40d4b74156bee84630b1b3009d
Source dataset
uspto-grants-1985_05
Patent number
US04518602

Reaction notes

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