4-Hydroxybenzaldehyde → HCID 18319102, compound

HRID 1383939Notes

Reaction equation

HRID 1383939 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.C(O)(=O)C.N1CCCCC1.[F:20][C:21]([F:26])([F:25])[C:22]([CH3:24])=[O:23]>O1CCCC1.C(OCC)(=O)C>[F:20][C:21]([F:26])([F:25])[C:22](=[O:23])/[CH:24]=[CH:6]/[C:5]1[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 176Acetic AcidHCID 8082PiperidineHCID 9871Methyl trifluoromethyl ketone2×

Product 1

HCID 18319102HCID 18319102, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-hydroxybenzaldehyde (5.0 g, 40.9 mmol) in tetrahydrofuran (165 ml) was treated with acetic acid (3.5 ml) and piperidine (3.5 ml). Then 1,1,1-trifluoroacetone (8 ml) was added dropwise. After 2 h at 22° C., another portion of 1,1,1-trifluoroacetone (8 ml) was added and the mixture was stirred for another 3 h. The reaction mixture was then diluted with ethyl acetate, washed with water, saturated ammonium chloride, saturated sodium bicarbonate, and brine. The organic phase was dried (magnesium sulfate), concentrated under reduced pressure and chromatographed on silica gel. Elution with a gradient of ethyl acetate (0-5%) in toluene gave 4.16 g (47%) of title material as yellow needles after crystallization from ether-hexane: mp 106-107° C.

Workup

  1. washwashed with water, saturated ammonium chloride, saturated sodium bicarbonate, and brine
  2. dry with materialThe organic phase was dried (magnesium sulfate)
  3. concentrationconcentrated under reduced pressure
  4. customchromatographed on silica gel
  5. washElution with a gradient of ethyl acetate (0-5%) in toluene

Sources & evidence

ORD record
ord-c3e09f98de5e465a986d81e739dd81ac
Source dataset
uspto-grants-2001_07
Patent number
US06255496B1

Reaction notes

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