3-Methoxybenzaldehyde → (9,10-Dihydro-anthracen-9-yl)-(3-methoxy-phenyl)-methanol

HRID 1454920Notes

Reaction equation

HRID 1454920 reaction equation
[CH:1]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Li]CCCC.[CH:20](=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1>C1COCC1>[CH:4]1[C:5]2[CH:6]([CH:20]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=3)[OH:29])[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:13][C:14]=2[CH:1]=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 115693-MethoxybenzaldehydeHCID 119409,10-DihydroanthraceneHCID 178418339Butyllithium

Product 1

HCID 57531220(9,10-Dihydro-anthracen-9-yl)-(3-methoxy-phenyl)-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cool a THF (50 mL) solution of 9,10-dihydroanthracene (5.10 g, 28 mmol) to 0° C. and add 1.6M n-BuLi (19 mL, 30 mmol) slowly. After 30 minutes, add m-anisaldehyde (3.4 mL, 28 mmol) to the dark brown solution. Allow the reaction to slowly warm to ambient temperature and then carefully quench with aqueous saturated NH4Cl. Shake the entire reaction with water/EtOAc and dry the organic layer (MgSO4). Concentrate under reduced pressure to give 9.4 g light tan oil. Purify by column chromatography using 25% EtOAc/hexane to give 4.7 g (53%) as a colorless oil that rapidly crystallized, mp 105.9° C. HPLC shows 94% purity.

Workup

  1. customthe reaction
  2. customcarefully quench with aqueous saturated NH4Cl
  3. customShake the entire reaction with water/EtOAc
  4. dry with materialdry the organic layer (MgSO4)
  5. concentrationConcentrate under reduced pressure
  6. customto give 9.4 g light tan oil
  7. customPurify by column chromatography
  8. customto give 4.7 g (53%) as a colorless oil
  9. customthat rapidly crystallized

Sources & evidence

ORD record
ord-22cc360e0b504006815ac71e4547afa8
Source dataset
uspto-grants-2009_01
Patent number
US07482344B2

Reaction notes

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