Methyl 4-Formylbenzoate → HCID 11776502, compound

HRID 1057588Notes

Reaction equation

HRID 1057588 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 3M 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 1M 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 1M 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-e26a5d061b774ba880a4be1280258fb7
Source dataset
uspto-grants-2003_02
Patent number
US06514985B1

Reaction notes

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