Sodium Sulfite → HCID 23703551, compound

HRID 226178Notes

Reaction equation

HRID 226178 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[S:12]([O-:15])([O-:14])=[O:13].[Na+:16].[Na+]>C(O)C.O>[CH2:10]([O:9][C:7](=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][S:12]([O-:15])(=[O:14])=[O:13])[CH3:11].[Na+:16]

Participants

5

Reactant 2

HCID 24437Sodium SulfiteHCID 117544Ethyl 6-bromohexanoate

Product 1

HCID 23703551HCID 23703551, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 6-bromohexanoate (61b) (2.48 g, 11.0 mmol) in ethanol (6 ml) a solution of sodium sulfite (2.16 g, 20.6 mmol) in water (9 ml) was added and the resulting mixture was refluxed for 1 hour. The reaction mixture was evaporated under reduced pressure and the obtained solid was extracted with boiling ethanol in Soxhlet extraction apparatus for 15-20 hours. The extract was evaporated and the residue was crystallised from ethanol-diethyl ether (1:10) giving the title compound (2.71 g, 99%) in a form of a white solid material. 1H NMR (DMSO-d6, HMDSO), δ: 1.05-1.78 (6H, m); 1.17 (3H, t, J=7.2 Hz); 2.26 (4H, t, J=7.5 Hz); 4.05 (2H, q, J=7.2 Hz).

Workup

  1. temperaturethe resulting mixture was refluxed for 1 hour
  2. customThe reaction mixture was evaporated under reduced pressure
  3. extractionthe obtained solid was extracted with boiling ethanol in Soxhlet extraction apparatus for 15-20 hours
  4. customThe extract was evaporated
  5. customthe residue was crystallised from ethanol-diethyl ether (1:10)

Sources & evidence

ORD record
ord-61b722730c6f43fe8151933077151a4e
Source dataset
uspto-grants-2009_07
Patent number
US07557140B2

Reaction notes

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