Toluene → HCID 70127065, compound

HRID 440620Notes

Reaction equation

HRID 440620 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]([OH:13])[CH:4]=1.[CH2:14]([C:23]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1)(O)[C:24]#[CH:25])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1.C1(C)C=CC=CC=1>CCCCCC>[CH2:14]([C:23]1([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[O:13][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:12]3[C:7]([C:6]=2[CH:25]=[CH:24]1)=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 151529324-Methoxynaphthalen-2-olHCID 570825081,1-Dianisylprop-2-yn-1-ol

Product 1

HCID 70127065HCID 70127065, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 4-methoxy-2-naphthol (0.26 g; 0.015 mol). 1,1-dianisylprop-2-yn-1-ol (0.40 g g;0.0015 mol), acidic alumina Brockmann 1 (3.5 g) and toluene (40.0 ml) was heated and stirred for 1.5 h, cooled, filtered. The filtrate was washed with 2M NaOH then water, dried and evaporated to give an orange gum. Trituration with hexane yielded 3,3-dianisyl-6-methoxy-3H-naphtho[2,1-b]pyran of formula (1) below as an off-white solid (41%). Crystallisation from hexane and ethylacetate gave the pyran as white micro-platelets, m.pt. 158°-160° C. ##STR8##

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. washThe filtrate was washed with 2M NaOH
  4. dry with materialwater, dried
  5. customevaporated
  6. customto give an orange gum

Sources & evidence

ORD record
ord-f8ad9acb69f340a8ae325d4d84b73cc5
Source dataset
uspto-grants-1996_05
Patent number
US05520853

Reaction notes

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