Sulfuric Acid → HCID 57804201, compound

HRID 2102882Notes

Reaction equation

HRID 2102882 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([OH:3])=[O:2].[CH2:12]([Mg]Cl)[CH:13]([CH3:15])[CH3:14].S(=O)(=O)(O)O>O1CCCC1.O>[CH3:12][CH:13]([CH3:15])/[CH:14]=[CH:8]/[C:7]1[CH:10]=[CH:11][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 120884-Formylbenzoic acidHCID 178418368HCID 178418368, compound

Product 1

HCID 57804201HCID 57804201, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-Carboxybenzaldehyde (1.0 g, 6.66 mmol) was dissolved in anhydrous tetrahydrofuran (50 mL) and cooled to 0° C. To the mixture was added isobutylmagnesium chloride (16 mL, 32 mmol, 2.0 M solution in THF). The reaction mixture was warmed to room temperature and stirred for 2 hours. The solution was acidified with 50% sulfuric acid in water and the THF was removed under vacuum. The aqueous phase was extracted twice with dichloromethane. The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated to give the desired compound (950 mg) as grey powder.

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. customthe THF was removed under vacuum
  3. extractionThe aqueous phase was extracted twice with dichloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-d2d8ec1e9046459b93037604f831167f
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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