Water → HCID 19347751, compound

HRID 1637150Notes

Reaction equation

HRID 1637150 reaction equation
[CH2:1](Cl)[C:2](=[CH2:4])[CH3:3].[CH3:6]C(C)([O-])C.[K+].[CH2:12]([OH:18])[C:13]1[O:17][CH:16]=[CH:15][CH:14]=1.O>CS(C)=O>[CH3:6][C:13]1([O:17][CH:16]=[CH:15][CH2:14]1)[CH2:12][O:18][CH2:1][C:2](=[CH2:4])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 7361Furfuryl AlcoholHCID 112413-Chloro-2-methyl-1-propeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 19347751HCID 19347751, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Methallyl chloride (0.85 M) was added to a solution of potassium t-butoxide (0.89 M) and furfuryl alcohol (0.89 M) in dimethyl sulfoxide (0.5 L). The exothermic reaction (~95° C.) was allowed to cool to room temperature over 2 hr and then added to 1.5 L water and extracted with 0.5 L ether. Crude product (125 g) was isolated from the ether phase and distilled at ~20 mm at 127° C. to yield 110 g (0.72 M) of methallyl 2-methylfurfuryl ether. Hydrosilylation of the methallyl group was accomplished by mixing with 0.93 M of dichloromethylsilane, 0.2 g of SIP6831.0 in xylene and heating to a gentle reflux. The reaction proceeded to completion with a brief vigorous reflux.

Workup

  1. customThe exothermic reaction (~95° C.)
  2. extractionextracted with 0.5 L ether
  3. customCrude product (125 g) was isolated from the ether phase
  4. distillationdistilled at ~20 mm at 127° C.

Sources & evidence

ORD record
ord-b7b4b3e45ad74d8da08e6729082712ec
Source dataset
uspto-grants-2000_03
Patent number
US06040115

Reaction notes

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