Benzoic acid, 3-formyl-4-hydroxy-, methyl ester → HCID 53256703, compound

HRID 1662418Notes

Reaction equation

HRID 1662418 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7])=[O:2].[CH:14]1([Mg]Br)[CH2:16][CH2:15]1>C1COCC1>[CH:14]1([CH:1]([OH:2])[C:3]2[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=2[OH:13])[C:6]([O:8][CH3:9])=[O:7])[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 212595Benzoic acid, 3-formyl-4-hydroxy-, methyl esterHCID 178418630HCID 178418630, compound

Product 1

HCID 53256703HCID 53256703, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In an ice-bath, methyl 3-formyl-4-hydroxybenzoate 66.38A (900 mg, 5 mmol) (commercially available from Aldrich) was dissolved in 5 mL THF. Then cyclopropylmagnesium bromide, 0.5 m in THF (22000 μL, 11 mmol) (commercially available from Aldrich) was added slowly. The reaction was raised to room temperature immediately and stirred at room temperature for 2 hours. After quenching with 1N HCl 11 mL, the reaction was extracted with EtOAc and dried. Silica gel chromatography afforded 950 mg of the product 66.38B (85%).

Workup

  1. customAfter quenching with 1N HCl 11 mL
  2. extractionthe reaction was extracted with EtOAc
  3. customdried

Sources & evidence

ORD record
ord-d7aeb708675445499ce4ba1211e35aa0
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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