Benzyl Chloride → 2-(Benzyloxy)-5-(tert-butyl)benzaldehyde

HRID 2401650Notes

Reaction equation

HRID 2401650 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].C([O-])([O-])=O.[K+].[K+].[CH2:20](Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CC(OC)(C)C>CN(C=O)C.O>[CH2:20]([O:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 15413tert-Butyl methyl etherHCID 14750905-tert-Butylsalicylaldehyde

Product 1

HCID 547951252-(Benzyloxy)-5-(tert-butyl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of compound 2 (614.5 g, 3.33 mol) in DMF (3.5 L) was added K2CO3 (953 g, 6.90 mol) and benzyl chloride (480 g, 3.80 mol). The mixture was heated to 90° C. and left stirring for 3 hours. The suspension was cooled to room temperature, then MTBE (2 L) was added, followed by water (12 L). The mixture was then stirred for 10 minutes and the aqueous layer was separated and extracted with MTBE (2 L×3). The organic layers were combined and washed with water (2 L×2) and brine (1.5 L×1) and concentrated to give compound 3 as a light-yellow solid. 1H NMR (DMSO-d6; 400 MHz) δ 10.42 (s), δ 7.71 (m), δ 7.51 (m), δ 7.43 (m), δ 7.35 (m), δ 7.24 (m), δ 5.27 (s), δ 1.26 (s).

Workup

  1. waitleft
  2. temperatureThe suspension was cooled to room temperature
  3. stirringThe mixture was then stirred for 10 minutes
  4. customthe aqueous layer was separated
  5. extractionextracted with MTBE (2 L×3)
  6. washwashed with water (2 L×2) and brine (1.5 L×1)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-647fda29d2d7486bab818c84bc5fd83b
Source dataset
uspto-grants-2014_08
Patent number
US08796308B2

Reaction notes

Loading…