Benzaldehyde → Ethyl 4-(alpha-hydroxybenzyl)benzoate

HRID 2183412Notes

Reaction equation

HRID 2183412 reaction equation
I[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.C([Mg]C(C)C)(C)C.[CH:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1.C(OC)(C)(C)C>[OH:27][CH:20]([C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 142891Ethyl 4-iodobenzoateHCID 178461729HCID 178461729, compound

Product 1

HCID 10244131Ethyl 4-(alpha-hydroxybenzyl)benzoateYield 90%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of 552 mg (2 mmol) of ethyl 4-iodobenzoate in 20 ml of THF was cooled to −40° C. and 1.06 mmol of diisopropylmagnesium in methyl tert-butyl ether were added. After 1 h at −40° C. 233 mg (2.2 mmol) of benzaldehyde were added. After 3 h, the reaction mixture was hydrolyzed and the org. phase was concentrated. Chromatography of the crude product with 4/1 pentane/ether afforded 460 mg (90%) of the alcohol.

Workup

  1. waitAfter 3 h
  2. concentrationphase was concentrated

Sources & evidence

ORD record
ord-8a4168880ee44c6cb5d5966673868e61
Source dataset
uspto-grants-2005_05
Patent number
US06899830B1

Reaction notes

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