Sodium Sulfite → HCID 23703551, compound

HRID 351084Notes

Reaction equation

HRID 351084 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 6bromohexanoate (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-54ed82e572fa49acbd1146384b3ea5e4
Source dataset
uspto-grants-2007_02
Patent number
US07183298B2

Reaction notes

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