Benzaldehyde → (3-[1,3]Dioxolan-2-ylphenyl)phenylmethanol

HRID 1371837Notes

Reaction equation

HRID 1371837 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.CCCCCC.[CH:24](=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1>[O:9]1[CH2:10][CH2:11][O:12][CH:8]1[C:4]1[CH:3]=[C:2]([CH:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[OH:31])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 8058HexaneHCID 873062-(3-Bromophenyl)-1,3-dioxolaneHCID 178418339Butyllithium

Product 1

HCID 10824966(3-[1,3]Dioxolan-2-ylphenyl)phenylmethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Combine 2-(3-bromophenyl)-1,3-dioxolane (10.0 ml, 66.0 mmol) and tetrahydrofuran (100 ml) and cool to about −78° C. Add dropwise a solution of n-butyllithium, 1.6 M solution in hexane (44.0 ml, 66.0 mmol). After 10 min, add a solution of benzaldehyde (7.6 ml, 66.0 mmol) in tetrahydrofuran (50 ml) via cannula. After 1 hour, warm to room temperature. After 18 hours, quench into water and extract with dichloromethane. Combine the organic layers and wash sequentially with distilled water and brine and then dry (Na2SO4), filter, and concentrate to give a residue. Chromatograph the residue eluting with 7:3 hexane:EtOAc to give the title compound.

Workup

  1. waitAfter 1 hour
  2. waitAfter 18 hours
  3. customquench into water
  4. extractionextract with dichloromethane
  5. washwash sequentially with distilled water and brine
  6. dry with materialdry (Na2SO4)
  7. filtrationfilter
  8. concentrationconcentrate
  9. customto give a residue
  10. washChromatograph the residue eluting with 7:3 hexane

Sources & evidence

ORD record
ord-70cd1c0920614208a8c92da74f201cf1
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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