Propanal → HCID 54392015, compound

HRID 1534269Notes

Reaction equation

HRID 1534269 reaction equation
[CH:1](=O)[CH2:2][CH3:3].[F:5][C:6]1([Li])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]1[F:12].CC1C=CC(S(O)(=O)=O)=CC=1.S(=O)(=O)(O)O>C1COCC1.C1(C)C=CC=CC=1.O.CO>[CH:1]([C:8]1[C:7]([F:12])=[C:6]([F:5])[CH:11]=[CH:10][CH:9]=1)=[CH:2][CH3:3]

Participants

9

Reactant 4

HCID 527PropanalHCID 1118Sulfuric AcidHCID 6101p-Toluenesulfonic acidHCID 178506772HCID 178506772, compound

Product 1

HCID 54392015HCID 54392015, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 0.13 mol of propionaldehyde in 30 ml of THF is added dropwise to the solution of 1,2-difluorophenyllithium in THF prepared according to 1b). The mixture is subsequently warmed to 0° C. and worked up as customary. The resulting crude product of the carbinol is dissolved in 80 ml of toluene and heated to boiling for 1 hour in a water separator with 1 g of p-TsOH. 0.2 ml of concentrated sulfuric acid are then added and the mixture is again heated for 1 hour, as above. It is then worked up as customary, b.p.30 : 105° C.

Workup

  1. customprepared
  2. temperatureheated
  3. temperaturethe mixture is again heated for 1 hour
  4. custom105° C.

Sources & evidence

ORD record
ord-e5e77c53de304d40a198a4105fbdbf44
Source dataset
uspto-grants-1992_02
Patent number
US05087764

Reaction notes

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