1-Chloromethylnaphthalene → HCID 19792504, compound

HRID 1655502Notes

Reaction equation

HRID 1655502 reaction equation
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].Cl[CH2:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1>>[C:10]1([CH2:9][CH2:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH2:5][CH2:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 68451-ChloromethylnaphthaleneHCID 31261Acetylacetone

Product 1

HCID 19792504HCID 19792504, compound

Procedure

Using 2,4-pentanedione (59.6 g, 0.595 mol) and 1-chloromethylnaphthalene (245 g), the reaction was carried out in the same manner as described in Example 17, (1), and the residual oil (200 g) was chromatographed on silica gel (Wako Gel C-200) with n-hexane/benzene (1:4) as eluent to give the title compound as a yellow oil which was an ca 1:6 mixture of Keto/Enol as seen by the methylene singlet at δ3.33 ppm and the methine singlet at δ5.27 ppm in the 1HNMR spectrum; yield: 71 g.

Workup

  1. customthe residual oil (200 g) was chromatographed on silica gel (Wako Gel C-200) with n-hexane/benzene (1:4) as eluent

Sources & evidence

ORD record
ord-cbffa0f8ee55416a8b8e54c8f3ceb8b0
Source dataset
uspto-grants-1993_10
Patent number
US05250669

Reaction notes

Loading…