Water → 4-(Benzyloxy)-3-chlorobenzaldehyde

HRID 1665706Notes

Reaction equation

HRID 1665706 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[CH:11]1[CH:16]=[CH:15][C:14]([CH2:17]Br)=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+].O>CC#N>[CH2:17]([O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[Cl:1])[C:14]1[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 170223-Chloro-4-hydroxybenzaldehyde

Product 1

HCID 27354954-(Benzyloxy)-3-chlorobenzaldehydeYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-chloro-4-hydroxy-benzaldehyde (5.0 g, 32 mmol) and BnBr (6.6 g, 38 mmol) in CH3CN (100 mL) was added K2CO3 (8.8 g, 64 mmol). The mixture was heated at reflux for 2 hours. The resulting mixture was poured into water (100 mL), and extracted with EtOAc (100 mL×3). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and evaporated under vacuum to give crude product, which was purified by column (petroleum ether/EtOAc 15:1) to give 4-benzyloxy-3-chloro-benzaldehyde (7.5 g, 95%). 1H NMR (CDCl3, 400 MHz) δ 9.85 (s, 1H), 7.93 (d, J=2.0 Hz, 1 H), 7.73 (dd, J=2.0, 8.4 Hz, 1 H), 7.47-7.34 (m, 5 H), 7.08 (d, J=8.8 Hz, 1 H), 4.26 (s, 2 H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. extractionextracted with EtOAc (100 mL×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated under vacuum
  7. customto give crude product, which
  8. customwas purified by column (petroleum ether/EtOAc 15:1)

Sources & evidence

ORD record
ord-04e44db4396d4949b3aaa66fd34bab78
Source dataset
uspto-grants-2011_10
Patent number
US08039491B2

Reaction notes

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