Furfural → HCID 54135160, compound

HRID 2057651Notes

Reaction equation

HRID 2057651 reaction equation
[Na+].CS([CH2-])=O.[Br-].[C:7]([CH2:10][CH2:11][CH2:12][CH2:13][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:9])=[O:8].[CH:33](=O)[C:34]1[O:38][CH:37]=[CH:36][CH:35]=1>CS(C)=O>[O:38]1[CH:37]=[CH:36][CH:35]=[C:34]1[CH:33]=[CH:13][CH2:12][CH2:11][CH2:10][C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 7362FurfuralHCID 161236(4-Carboxybutyl)triphenylphosphonium bromideHCID 10154010Methane, sulfinylbis-, ion(1-), sodium

Product 1

HCID 54135160HCID 54135160, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a cooled solution of dimsyl sodium (prepared by heating 4.35 g. of 50% oil dispersion of sodium hydride in 50 ml. dimethylsulfoxide at 60° for 2 hours under argon) is added dropwise 20.0 g. of (4-carboxybutyl)triphenylphosphonium bromide in 90 ml. dimethylsulfoxide. After the solution has stirred at room temperature for one hour, a solution of 4.34 g. furfural in 20 ml. dimethylsulfoxide is added dropwise to the cool (15°) solution over 20 minutes. After 2 hours the dimethylsulfoxide is evaporated, the residue is dissolved in 100 ml. water, filtered and extracted four times with 150 ml. portions of ethyl acetate. The aqueous solution is acidified to pH 1 with 1 N hydrochloric acid, saturated with sodium chloride and extracted twice with 150 ml. portions of ethyl ether. The ether is dried and evaporated to yield the title compound as a yellow oil.

Workup

  1. temperaturecool (15°) solution over 20 minutes
  2. customAfter 2 hours the dimethylsulfoxide is evaporated
  3. dissolutionthe residue is dissolved in 100 ml
  4. filtrationwater, filtered
  5. extractionextracted four times with 150 ml
  6. extractionextracted twice with 150 ml
  7. dry with materialThe ether is dried
  8. customevaporated

Sources & evidence

ORD record
ord-167f0ccec1174fd9884c992d609b2a5c
Source dataset
uspto-grants-1980_07
Patent number
US04211783

Reaction notes

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