Methyl 4-Formylbenzoate → HCID 11776502, compound

HRID 2120848Notes

Reaction equation

HRID 2120848 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:9]([C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)=[O:10]>>[OH:10][CH:9]([C:11]1[CH:12]=[CH:13][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:19][CH:20]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 15294Methyl 4-FormylbenzoateHCID 178418255HCID 178418255, compound

Product 1

HCID 11776502HCID 11776502, compound

Procedure

Under a nitrogen atmosphere phenyl magnesium bromide (39 mL of 3 M in ether) was added via a syringe over a period of 30 minutes to a solution of methyl 4-formylbenzoate (19.2 g, 117 mmol). The mixture was allowed to stir for an additional 10 minutes and then it was quenched by the addition of 1 M hydrochloric acid (125 mL). The reaction mixture was extracted with diethyl ether (2×200 mL). The combined extracts were washed with brine, dried over magnesium sulfate, filtered and then concentrated under vacuum to provide a yellow oil. This material was purified by flash chromatography (silica gel eluting with 6:1 hexanes:ethyl acetate) to provide 6.9 g of methyl 4-(α-hydroxybenzyl)benzoate as a clear oil.

Workup

  1. customit was quenched by the addition of 1 M hydrochloric acid (125 mL)
  2. extractionThe reaction mixture was extracted with diethyl ether (2×200 mL)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto provide a yellow oil
  8. customThis material was purified by flash chromatography (silica gel eluting with 6:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-4780dc9ce5a34101945c7de7d4459cbf
Source dataset
uspto-grants-2004_02
Patent number
US06693113B2

Reaction notes

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