Hydrochloric Acid → 3-(10H-Anthracen-9-ylidenemethyl)-phenol

HRID 1454922Notes

Reaction equation

HRID 1454922 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[CH:6]=[C:7]1[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2.Cl.N1C=CC=CC=1.Cl>>[CH:19]1[C:20]2[C:7](=[CH:6][C:5]3[CH:4]=[C:3]([OH:2])[CH:23]=[CH:22][CH:21]=3)[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:14][C:15]=2[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10176127Pyridinium chlorideHCID 575312189-(3-Methoxy-benzylidene)-9,10-dihydro-anthracene

Product 1

HCID 575312033-(10H-Anthracen-9-ylidenemethyl)-phenolYield 84.4%

Conditions

Temperature
220 °C

Procedure

Mix 9-(3-methoxy-benzylidene)-9,10-dihydro-anthracene (900 mg, 3.0 mmol) and pyridine hydrochloride (4 g) and heat at 220° C. for 30 minutes. Cool to 115° C. and carefully add 5N HCl. Extract the product into EtOAc, dry (MgSO4) the organic solution and concentrate to give 720 mg dark oil. Purify by ISCO using EtOAc/hexanes to give title compound, mp 195.8° C., HPLC>99% purify. MS (es) 283 (M−1). 1H NMR (DMSO -d6) □3.74 (br s, 1H), 6.79-7.45 (m, 13H), 9.46 (s, 1H); 13C NMR (DMSO-d6) δ 40.22, 114.59, 115.81, 119.51, 125.53, 125.85, 127.02, 127.30, 128.05, 128.27, 128.56, 129.77, 129.06, 129.39, 134.75, 135.83, 138.98, 139.92, 142.87, 144.63, 157.27

Workup

  1. temperatureCool to 115° C.
  2. extractionExtract the product into EtOAc
  3. dry with materialdry (MgSO4) the organic solution
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-d65e01f125dd4153920558b6128a7a4d
Source dataset
uspto-grants-2009_01
Patent number
US07482344B2

Reaction notes

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