4-Hydroxybenzaldehyde → HCID 19382483, compound

HRID 2400193Notes

Reaction equation

HRID 2400193 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10]1([CH2:16][CH2:17][CH2:18][Mg]Br)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1>[OH:7][CH:6]([C:5]1[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=1)[CH2:18][CH2:17][CH2:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 178418471HCID 178418471, compound

Product 1

HCID 19382483HCID 19382483, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a 0° C. solution of 4-hydroxybenzaldehyde (6.1 g) in THF (75 mL) is added a 3.6 M ethereal solution of 3-phenylpropyl-magnesium bromide (30.5 mL). The resulting suspension was stirred at 25° C. for 16 hrs. and then transferred slowly into ice cold 25% aqueous NH4OAc. The product was extracted into EtOAc (3×100 mL) and the combined extracts were washed with brine, dried with MgSO4 and the solvents were removed under reduced pressure. The residue was swished in a 1:5 mixture of EtOAc and hexanes for 2 hrs. and the solid was filtered and dried to yield the title compound.

Workup

  1. extractionThe product was extracted into EtOAc (3×100 mL)
  2. washthe combined extracts were washed with brine
  3. dry with materialdried with MgSO4
  4. customthe solvents were removed under reduced pressure
  5. additionThe residue was swished in a 1:5 mixture of EtOAc and hexanes for 2 hrs
  6. filtrationand the solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-c99fa1429ceb44cea9e5bb312b69645f
Source dataset
uspto-grants-1995_09
Patent number
US05453443

Reaction notes

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