Citric Acid → 4-Benzylbenzaldehyde

HRID 68227Notes

Reaction equation

HRID 68227 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:9]([C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1)=[O:10].C(=O)([O-])[O-].[K+].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[CH2:1]([C:14]1[CH:15]=[CH:16][C:11]([CH:9]=[O:10])=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 498864-BenzylbenzaldehydeYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Benzyl bromide (41 g, 240 mmol), 4-formylbenzeneboronic acid (28 g, 186.7 mmol), palladium tetrakis triphenyl phosphine (7.9 g, 6.84 mmol) and potassium carbonate (84.7 g, 613 mmol) were combined in tetrahydrofuran (620 mL) and heated at 80° C. under nitrogen for 8 hours. The resulting suspension was allowed to cool to ambient temperature and stirred overnight. The reaction mixture was poured into 10% citric acid (50 mL) and extracted with ethyl acetate (3-fold 50 mL). The combined organic extracts were washed with brine (100 mL) and dried (magnesium sulphate) and the solvent removed in vacuo. The resulting oil was purified by column chromatography on silica gel eluting with ethyl acetate:heptane, (0:1 changing to 1:5, by volume) to give the title compound as a colourless oil, 83% yield, 30.45 g.

Workup

  1. temperatureto cool to ambient temperature
  2. extractionextracted with ethyl acetate (3-fold 50 mL)
  3. washThe combined organic extracts were washed with brine (100 mL)
  4. dry with materialdried (magnesium sulphate)
  5. customthe solvent removed in vacuo
  6. customThe resulting oil was purified by column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-88e9b5916c4b4a1eaa9fc78604d5ac0e
Source dataset
uspto-grants-2014_09
Patent number
US08822439B2

Reaction notes

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