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

HRID 1666780Notes

Reaction equation

HRID 1666780 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-b97f532aec3147cd866427200825d405
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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