Chloroform → 4-(2-Benzoyloxyethyl)benzaldehyde

HRID 2116494Notes

Reaction equation

HRID 2116494 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.C(Cl)(Cl)Cl.C(N(CC)CC)C.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C1C=CN=CC=1.O.C(OCC)(=O)C>[C:23]([O:1][CH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 4

HCID 6212ChloroformHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 184247214-(2-Hydroxyethyl)benzaldehyde

Product 1

HCID 229349784-(2-Benzoyloxyethyl)benzaldehydeYield 50.3%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Next, to a mixture of 4-(2-hydroxyethyl)benzaldehyde (6.3 g, 42.2 mmol) and chloroform (170 mL), triethylamine (5.1 g, 50.6 mmol), benzoyl chloride (7.1 g, 50.6 mmol) and 4-dimethylaminopyridine (515 mg, 4.2 mmol) were added at 0° C. The reaction mixture was stirred at room temperature for 2 hours, poured into a mixture of ethyl acetate and water, and then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. After concentration, the resulting residue was purified by neutral silica gel column chromatography (hexane:ethyl acetate=20:1 to 10:1) to give 4-(2-benzoyloxyethyl)benzaldehyde (5.4 g).

Workup

  1. additionwere added at 0° C
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationAfter concentration
  6. customthe resulting residue was purified by neutral silica gel column chromatography (hexane:ethyl acetate=20:1 to 10:1)

Sources & evidence

ORD record
ord-9432e7691b494c2c8cce8fe16d65d97c
Source dataset
uspto-grants-2008_10
Patent number
US07439232B2

Reaction notes

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