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

HRID 440621Notes

Reaction equation

HRID 440621 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. ##STR10##

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-d38d92d26a1448f587da03990a070ffd
Source dataset
uspto-grants-1996_05
Patent number
US05520853

Reaction notes

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