2-Chlorotoluene → HCID 10020292, compound

HRID 375006Notes

Reaction equation

HRID 375006 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:17])(C)[CH:6]([CH:15]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O.Cl[C:19]1C=CC(OC)=CC=1.C1(C)C(Cl)=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:39](OCC)(=[O:46])[CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42].N12CCCN=C1CCCCC2>ClC(Cl)C(Cl)Cl>[CH2:44]([O:43][C:41]([C:40]1[C:39](=[O:46])[O:17][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:15][C:6]=2[C:7]=1[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=1[CH3:19])=[O:42])[CH3:45]

Participants

8

Reactant 6

HCID 72382-ChlorotolueneHCID 7761Diethyl MalonateHCID 121674-ChloroanisoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 6451240Aluminum(III) ChlorideHCID 18996302HCID 18996302, compound

Product 1

HCID 10020292HCID 10020292, compound

Reagents, catalysts & solvents 1

HCID 65911,1,2,2-TetrachloroethaneSolvent

Procedure

A mixture of 5-Chloro-2-hydroxy-2-methylbenzophenone [prepared by reaction of 4-chloroanisole with ortho-tolyl chloride in 1,1,2,2,-tetrachloroethane in the presence of aluminum chloride (150° C., 7 hours): melting point 65°-66° C.] (71.9 g), diethyl malonate (70 ml) and 1,8diazabicyclo[5.4.0]undec-7-ene (4 ml) was stirred at 170° C. for 6 hours. The reaction mixture was purified by silica gel column chromatography (hexane) to yield 6-chloro-4-(2-methylphenyl)-2-oxo-2H-1-benzopyran-3-carboxylic acid ethyl ester as colorless crystals (73.2 g).

Workup

  1. customThe reaction mixture was purified by silica gel column chromatography (hexane)

Sources & evidence

ORD record
ord-e2b5fca72e31491097efbf5fc500c650
Source dataset
uspto-grants-1996_01
Patent number
US05482967

Reaction notes

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