Sulfuric Acid → HCID 19892495, compound

HRID 893392Notes

Reaction equation

HRID 893392 reaction equation
[Mg].[CH2:2](Br)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:10]1([O:15][C:16]2[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=2[O:24][CH3:25])[CH:19]=[O:20])[CH2:14][CH2:13][CH2:12][CH2:11]1.OS(O)(=O)=O>C(OCC)C>[CH:10]1([O:15][C:16]2[CH:17]=[C:18]([CH:19]([OH:20])[CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH:21]=[CH:22][C:23]=2[O:24][CH3:25])[CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7498Benzyl Bromide3×HCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 5462224Magnesium

Product 1

HCID 19892495HCID 19892495, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent4×

Procedure

To a magnetically-stirred solution of freshly crushed magnesium turnings (36.54 mmol, 0.888 g) in anhydrous ethyl ether (20 mL) at room temperature is added a solution of benzyl bromide (36.54 mmol, 4.35 mL) in anhydrous ethyl ether (15 mL) dropwise via addition funnel. The addition is slow at first; only 2 to 3 mL of reagent is added and the reaction mixture is heated until gas evolution is observed. Dropwise addition of benzyl bromide is begun at this point, and the reaction mixture is diluted with ethyl ether (20 mL) to prevent dimerization of the Grignard reagent. Once the addition of benzyl bromide is complete, the reaction is allowed to stir at room temperature for 1 hour and then a solution of 3-cyclopentyloxy-4-methoxybenzaldehyde (30.00 mmol, 6.61 g) in anhydrous ethyl ether (30 mL) is added dropwise at room temperature. The reaction mixture is allowed to stir at room temperature for 30 minutes and then poured into a solution of ice water (500 mL) containing concentrated H2SO4 (7 mL). The aqueous mixture is extracted with ethyl acetate (2×300 mL) and the combined organic layers are washed with saturated NaHCO3 (300 mL). The organic layer is dried (Na2SO4) and concentrated in vacuo to afford the title compound as a white solid (25.97 mmol, 8.06 g; 86%) of sufficient purity to be used directly in subsequent transformation.

Workup

  1. additiondropwise via addition funnel
  2. additionThe addition
  3. temperaturethe reaction mixture is heated until gas evolution
  4. stirringto stir at room temperature for 30 minutes
  5. extractionThe aqueous mixture is extracted with ethyl acetate (2×300 mL)
  6. washthe combined organic layers are washed with saturated NaHCO3 (300 mL)
  7. dry with materialThe organic layer is dried (Na2SO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c1f3706f952b48c59f59204ff3535102
Source dataset
uspto-grants-1992_06
Patent number
US05124455

Reaction notes

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