1-Naphthaldehyde → HCID 11043648, compound

HRID 366356Notes

Reaction equation

HRID 366356 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.[C:10]1([CH:20]=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1>C1COCC1>[CH3:9][O:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[CH:20]([OH:21])[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 61951-NaphthaldehydeHCID 169713-Bromoanisole

Product 1

HCID 11043648HCID 11043648, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromoanisole (5.61 g, 30.0 mmol) in dry THF (80 mL) was dropwise added n-butyl lithium-hexane solution (1.6 M, 37.5 mL, 60 mmol) under nitrogen at -78° C. The reaction mixture was allowed to warm to r.t. in 2 h and cooled down again to -78° C. prior to addition of 1-naphthaldehyde (4.69 g, 30.0 mmol, in 10 mL THF). The mixture was warmed to r.t. in 3 h, and then quenched with aqueous NH4Cl solution, extracted with ethyl acetate (3×50 mL). The combined organic phases were washed with brine, dried over MgSO4. Removal of solvents in vacuo provided 3-methoxy-α-(1-naphthyl)benzyl alcohol (4.25 g, 54%). GC-MS (Rt =10.41 min) 264 (M+), 245, 231, 215, 202, 155, 135, 128, 109.

Workup

  1. customat -78° C
  2. temperaturecooled down again to -78° C.
  3. temperatureThe mixture was warmed to r.t. in 3 h
  4. customquenched with aqueous NH4Cl solution
  5. extractionextracted with ethyl acetate (3×50 mL)
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over MgSO4
  8. customRemoval of solvents in vacuo

Sources & evidence

ORD record
ord-2e782a1186c14e1099a50d6a1430eaab
Source dataset
uspto-grants-2000_10
Patent number
US06130222

Reaction notes

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