2-Naphthol → 3,3-dianisyl-3H-naphtho[2,1-b]pyran

HRID 54604Notes

Reaction equation

HRID 54604 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].[CH2:12]([C:21]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)(O)[C:22]#[CH:23])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[CH2:12]([C:21]1([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[O:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10]([C:1]=2[CH:23]=[CH:22]1)=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:13]1[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 86632-NaphtholHCID 570825081,1-Dianisylprop-2-yn-1-ol

Product 1

HCID 701290743,3-dianisyl-3H-naphtho[2,1-b]pyranYield 66%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-naphthol (3.23 g;0.0224 mol), 1,1-dianisylprop-2-yn-1-ol (6.00 g;0.0224 mol), acidic alumina Brockmann 1(6 g) and toluene (250 ml) was heated and stirred for 1.5 h, cooled, filtered and the solid washed with toluene. The filtrate was evaporated to give a pale purple tacky solid which was washed with pet. ether (40-60)/diethyl ether to yield crude product (7.07 g). Purification of the solid by crystallisation from ethylacetate gave 3,3-dianisyl-3H-naphtho[2,1-b]pyran as a white solid (5.52 g;66% yield), m.pt 176°-177° C. ##STR24##

Workup

  1. temperaturewas heated
  2. temperaturecooled
  3. filtrationfiltered
  4. washthe solid washed with toluene
  5. customThe filtrate was evaporated
  6. customto give a pale purple tacky solid which
  7. washwas washed with pet. ether (40-60)/diethyl ether
  8. customto yield crude product (7.07 g)
  9. customPurification of the solid
  10. customby crystallisation from ethylacetate

Sources & evidence

ORD record
ord-4a80bfb023df4bb28e5fcb2203312986
Source dataset
uspto-grants-1997_04
Patent number
US05623005

Reaction notes

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