N,N-Dimethylaniline → HCID 19375799, compound

HRID 2211385Notes

Reaction equation

HRID 2211385 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([CH:19]=[CH:20][CH:21]=1)[O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1)C=C.CN(C)[C:24]1[CH:29]=CC=C[CH:25]=1>C(OCC)(=O)C>[CH2:29]([C:21]1[CH:20]=[CH:19][C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:17][CH:18]=2)=[CH:6][C:5]=1[OH:4])[CH:24]=[CH2:25]

Participants

4

Reactant 2

HCID 949N,N-DimethylanilineHCID 19375796Methyl 4-{3-[(prop-2-en-1-yl)oxy]phenoxy}benzoate

Product 1

HCID 19375799HCID 19375799, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 4-(3-allyloxyphenoxy)benzoate in N,N-dimethylaniline was heated at 190° C. for 19 hours, cooled, diluted with ethyl acetate, washed with aqueous hydrochloric acid, dried, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with hexane/ethyl ether to give a 40:60 mixture of the title compounds as an oil in 92% yield. NMR.

Workup

  1. temperaturecooled
  2. washwashed with aqueous hydrochloric acid
  3. customdried
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with hexane/ethyl ether
  6. customto give

Sources & evidence

ORD record
ord-429bfc0a93ec4f019d89a38b1c45c279
Source dataset
uspto-grants-1995_10
Patent number
US05462954

Reaction notes

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