Benzyl Chloride → 3,5-Difluoro-2,4-dibenzyloxybenzaldehyde

HRID 355409Notes

Reaction equation

HRID 355409 reaction equation
[F:1][C:2]1[C:3](O)=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1[OH:10])[CH:5]=[O:6].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:21]([O-:24])([O-])=O.[K+].[K+]>CC(C)=O>[F:1][C:2]1[C:3]([O:24][CH2:21][C:2]2[CH:3]=[CH:4][CH:7]=[CH:8][CH:9]=2)=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1[O:10][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 189423273,5-Difluoro-2,4-dihydroxybenzaldehyde

Product 1

HCID 189423223,5-Difluoro-2,4-dibenzyloxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a 0.1M solution of Compound 13 (1.0 eq) in acetone is added benzyl chloride (4.0 eq) and anhydrous K2CO3 (7.0 eq). The mixture is heated to reflux for 8 hours and filtered. The filtrate is concentrated in vacuo, and the residue is dissolved in EtOAc. The resulting solution is washed with 3% HCl, washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue is recrystallized from MeOH to yield Compound 23.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 8 hours
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated in vacuo
  5. dissolutionthe residue is dissolved in EtOAc
  6. washThe resulting solution is washed with 3% HCl
  7. washwashed with brine
  8. dry with materialdried over anhydrous MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe residue is recrystallized from MeOH

Sources & evidence

ORD record
ord-859e2011bfca461496c39b018267b274
Source dataset
uspto-grants-1998_11
Patent number
US05830912

Reaction notes

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