2,3-Dimethylanisole → HCID 12704542, compound

HRID 1415198Notes

Reaction equation

HRID 1415198 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[Cl:11][C:12]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=1[O:19][CH3:20].[CH3:21][C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[O:29][CH3:30].ClC1C(Cl)=C(OC)C=CC=1[CH2:41][CH2:42][CH2:43][C:44]([OH:46])=[O:45]>>[CH3:8][C:7]1[C:2]([CH3:1])=[C:3]([O:9][CH3:10])[CH:4]=[CH:5][C:6]=1[C:41]([CH2:42][CH2:43][C:44]([OH:46])=[O:45])=[O:19].[Cl:28][C:27]1[C:22]([CH3:21])=[C:23]([O:29][CH3:30])[CH:24]=[CH:25][C:26]=1[C:41]([CH2:42][CH2:43][C:44]([OH:46])=[O:45])=[O:9].[CH3:18][C:17]1[C:12]([Cl:11])=[C:13]([O:19][CH3:20])[CH:14]=[CH:15][C:16]=1[C:41]([CH2:42][CH2:43][C:44]([OH:46])=[O:45])=[O:9]

Participants

7

Reactant 4

HCID 762692,3-DimethylanisoleHCID 767493-Chloro-2-methylanisoleHCID 21483921HCID 21483921, compoundHCID 21980608HCID 21980608, compound

Product 3

HCID 12704542HCID 12704542, compoundHCID 21483927HCID 21483927, compoundHCID 21483945HCID 21483945, compound

Procedure

It is equally suitable to employ an equimolar amount of 2,3-dimethylanisole, or 2-halo-3-methylanisoles such as 2-chloro-3-methylanisole; and 2-methyl-3-haloanisoles such as 2-methyl-3-chloroanisole in Step 1 in place of the 2,3-dichloroanisole used therein to obtain the corresponding 3-(2,3-dimethyl-4-methoxybenzoyl)propionic acid, 3-(2-chloro-3-methyl-4-methoxybenzoyl)propionic acid and 3-(2-methyl-3-chloro-4-methoxybenzoyl)propionic acid, which, in turn, are used in equimolar amount to substitute for the 3-(2,3-dichloro-4-methoxybenzoyl)propionic acid used in Step 2 to obtain the corresponding 4-(2,3-dimethyl-4-methoxyphenyl)butyric acid, 4-(2-chloro-3-methyl-4-methoxyphenyl)butyric acid; and 4-(2-methyl-3-chloro-4-methoxyphenyl)butyric acid.

Sources & evidence

ORD record
ord-8ccf59b62d324be0aa3c9bddd71b8e7c
Source dataset
uspto-grants-1977_01
Patent number
US04003927

Reaction notes

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