3-Methoxyphenol → 1,3-Dimethyl-4-(m-methoxyphenyloxy)-benzene

HRID 1605170

Reaction equation

HRID 1605170 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[C:4]([CH3:9])[CH:3]=1.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1.CN(C)C(=O)N(C)C.CN1CCCC1=O>O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:18][C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([O:11][CH3:10])[CH:13]=2)=[C:4]([CH3:9])[CH:3]=1

Participants

6

Reactant 4

HCID 90073-MethoxyphenolHCID 12437TetramethylureaHCID 13387N-methyl-2-pyrrolidoneHCID 68503Benzene, 1-bromo-2,4-dimethyl-

Product 1

HCID 215496571,3-Dimethyl-4-(m-methoxyphenyloxy)-benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1,3-dimethyl-4-bromobenzene, 10.5 g. of m-methoxyphenol, 4.65 g. of cuprous oxide, 40 ml. of tetramethylurea, and 75 ml. of N-methylpyrrolidone is stirred at 165° for 96 hours. The resultant mixture is diluted with water and extracted with methylene chloride. The methylene chloride extracts are chromatographed on 300 g. of alumina with gradient elution using hexane:ether to give 1,3-dimethyl-4-(m-methoxyphenyloxy)-benzene.

Workup

  1. extractionextracted with methylene chloride
  2. customThe methylene chloride extracts are chromatographed on 300 g
  3. washof alumina with gradient elution

Sources & evidence

ORD record
ord-6b639ce2671f4045b8a7ddbf95e838ee
Source dataset
uspto-grants-1976_04
Patent number
US03949084

Linked notes

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