(3,4-Dimethoxyphenyl)acetic acid → HCID 371217, compound

HRID 1605194Notes

Reaction equation

HRID 1605194 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1.C[O:25]C1C=C(C)C=CC=1OC.C(=O)C1C=CC(OC)=C(OC)C=1.[CH3:47][O:48][C:49]1[CH:50]=[C:51]([CH2:57][C:58]([OH:60])=O)[CH:52]=[CH:53][C:54]=1[O:55][CH3:56].[Cl-:61].[Al+3].[Cl-].[Cl-]>C(=S)=S>[CH3:47][O:48][C:49]1[CH:50]=[C:51]([CH2:57][C:58]([Cl:61])=[O:60])[CH:52]=[CH:53][C:54]=1[O:55][CH3:56].[CH3:11][O:10][C:5]1[C:6]([O:8][CH3:9])=[CH:7][C:2]([CH3:1])=[C:3]([C:12](=[O:25])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)[CH:4]=1

Participants

8

Reactant 5

HCID 7139(3,4-Dimethoxyphenyl)acetic acidHCID 8419VeratraldehydeHCID 681263,4-Dimethoxytoluene2×HCID 6451240Aluminum(III) ChlorideHCID 21546504HCID 21546504, compound

Product 2

HCID 371217HCID 371217, compoundHCID 3604458(3,4-Dimethoxyphenyl)acetyl chloride

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

In the preparation of 2-methyl-3',4,4' , 5-tetramethoxybibenzyl, for example, 3,4-dimethoxytoluene was prepared from commercial veratraldehyde by the method of Bruce and Sutcliff, J. Chem. Soc., 3824 (1956). 3,4-Dimethoxyphenylacetyl chloride was prepared from commercial 3,4-dimethoxyphenylacetic acid and added to a stirred mixture of 3,4-dimethoxytoluene and aluminum chloride in carbon disulfide. After reaction, the previously unknown 4,5-dimethoxy-2-(3,4-dimethoxyphenylacetyl) toluene was isolated (based upon the 3,4-dimethoxyphenyl acetic acid) and converted by a modified Wolff-Kishner reaction to 2-methyl-3',4,4',5-tetramethoxybibenzyl.

Workup

  1. customAfter reaction

Sources & evidence

ORD record
ord-0e3306f0aefa494c9904a1c030da140f
Source dataset
uspto-grants-1976_04
Patent number
US03950236

Reaction notes

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