Sulfuric Acid → 9-(3-Methoxy-benzylidene)-9,10-dihydro-anthracene

HRID 1454921Notes

Reaction equation

HRID 1454921 reaction equation
[CH:1]1[C:14]2[CH:13]([CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=3)O)[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.S(=O)(=O)(O)O>CC(O)=O>[CH3:24][O:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[CH:15]=[C:13]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][C:5]2[C:14]1=[CH:1][CH:2]=[CH:3][CH:4]=2

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 57531220(9,10-Dihydro-anthracen-9-yl)-(3-methoxy-phenyl)-methanol

Product 1

HCID 575312189-(3-Methoxy-benzylidene)-9,10-dihydro-anthraceneYield 123.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Add 4. 1 g (13 mmol) of (9,10-dihydro-anthracen-9-yl)-(3-methoxy-phenyl)-methanol to HOAc (75 mL) containing sulfuric acid (2 mL). Reflux for 2 h and pour into 1.2L ice water. Extract the product into EtOAc and wash with dilute NaOH. Dry (MgSO4) the organic solution, and concentrate to give 4.8 g dark oil. Purify on the ISCO using EtOAc/hexane to give 1.12 g (29%) title compound as a colorless oil. HPLC shows >95% purity. 1H NMR (CDCl3) δ3.87 (s, 2H), 3.92 (s, 3H), 6.89-7.47 (m, 13H); MS (CI) 298 (M).

Workup

  1. additionAdd 4
  2. temperatureReflux for 2 h
  3. extractionExtract the product into EtOAc
  4. washwash with dilute NaOH
  5. dry with materialDry (MgSO4) the organic solution
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-d585ff38e0e64ec68b012c6bed3b4288
Source dataset
uspto-grants-2009_01
Patent number
US07482344B2

Reaction notes

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