Benzyl Alcohol → HCID 70921751, compound

HRID 2365919Notes

Reaction equation

HRID 2365919 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[C:15](F)=[CH:14][C:13]=1F.Cl>O1CCCC1>[CH2:3]([O:10][C:13]1[CH:14]=[C:15]([O:10][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:16]([N+:18]([O-:20])=[O:19])=[CH:17][C:12]=1[F:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 750121,2,4-Trifluoro-5-nitrobenzene

Product 1

HCID 70921751HCID 70921751, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.82 g (70.6 mmol, 2.5 eq) of sodium hydride at 60% are added to a solution of 7.6 g (70.6 mmol, 2.5 eq) of benzyl alcohol in 100 ml of tetrahydrofuran. The reaction medium is stirred at ambient temperature for 1½ hours and then 5.0 g (28.2 mmol, 1 eq) of 1,2,4-trifluoro-5-nitrobenzene in solution in 50 ml of tetrahydrofuran are added dropwise. The reaction medium is refluxed for 3 hours. The reaction medium is treated with 150 ml of 1M hydrochloric acid and extracted with ethyl acetate. The organic phases are combined, washed with a saturated solution of sodium chloride, dried over magnesium sulphate, filtered and evaporated. The residue is chromatographed on silica gel, elution being carried out with 90/10 heptane/ethyl acetate.

Workup

  1. temperatureThe reaction medium is refluxed for 3 hours
  2. extractionextracted with ethyl acetate
  3. washwashed with a saturated solution of sodium chloride
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-b11220fafd604b099d047444dbb673c5
Source dataset
uspto-grants-2014_04
Patent number
US08697726B2

Reaction notes

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