Benzyl Chloride → HCID 57857232, compound

HRID 503658Notes

Reaction equation

HRID 503658 reaction equation
O[C:2]1[C:3]([OH:12])=[C:4]([C:7]([CH2:10][CH3:11])=[CH:8][CH:9]=1)[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+]>CN(C=O)C.CCOC(C)=O>[CH2:13]([O:12][C:3]1[CH:2]=[C:9]([O:24][CH2:21][C:2]2[CH:3]=[CH:4][CH:7]=[CH:8][CH:9]=2)[CH:8]=[C:7]([CH2:10][CH3:11])[C:4]=1[CH:5]=[O:6])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 86633812HCID 86633812, compound

Product 1

HCID 57857232HCID 57857232, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.9 g of dihydroxy-6-ethylbenzaldehyde, 3.48 ml of benzyl chloride and 4.7 g of K2CO3 are stirred in 5.2 ml of DMF at 90° for 2 h. The batch is diluted with EtOAc and washed with water. The organic phase is dried using Na2SO4, evaporated and chromatographed on silica gel. The uniform fractions are combined and evaporated. The oily residue solidifies on standing after a few days. Treatment with etheropetroleum ether 1:1 gives 3.5 g (88%) of 2,4-bisbenzyloxy-6-ethylbenzaldehyde, which discolours in air.

Workup

  1. washwashed with water
  2. customThe organic phase is dried
  3. customevaporated
  4. customchromatographed on silica gel
  5. customevaporated
  6. waiton standing after a few days

Sources & evidence

ORD record
ord-465d62122408421d8214a78aa8e8fb96
Source dataset
uspto-grants-2010_08
Patent number
US07776920B2

Reaction notes

Loading…