Anisole → HCID 22408243, compound

HRID 439792Notes

Reaction equation

HRID 439792 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[CH3:10][O:11][C:12](=[O:22])[C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=1.[Cl-].[Al+3].[Cl-].[Cl-]>>[CH3:10][O:11][C:12]([C:13]1[CH:21]=[CH:20][C:16]([C:17]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[O:7][CH3:8])=[O:18])=[CH:15][CH:14]=1)=[O:22]

Participants

4

Reactant 3

HCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 53442854Terephthalic acid monomethylester chloride

Product 1

HCID 22408243HCID 22408243, compound

Procedure

To a mixture of anisole (216 g) and terephtalic acid-methyl ester-chloride (99 g) was added aluminium chloride (200 g) at 0° C. in an amount of 1/3 to 1/4 at a time. In that case, temperature was kept to 25° C. or less, and it took from 45 minutes to 1 hour for addition. The temperature returned to room temperature after 30 minutes from termination of addition, and after stirring for 1.5 hours to 2 hours, the pink colored precipitate was obtained by pouring ice-water. The precipitate was separated by filtration, dried with water and washed with methanol. Methanol washings were concentrated under reduced pressure, and washed with a small amount of methanol to give the title compound.

Workup

  1. customwas kept to 25° C. or less
  2. additionit took from 45 minutes to 1 hour for addition
  3. additionThe temperature returned to room temperature after 30 minutes from termination of addition
  4. customthe pink colored precipitate was obtained
  5. customThe precipitate was separated by filtration
  6. dry with materialdried with water
  7. washwashed with methanol
  8. concentrationMethanol washings were concentrated under reduced pressure
  9. washwashed with a small amount of methanol

Sources & evidence

ORD record
ord-f9d5ff58be07450497194a7b32872c48
Source dataset
uspto-grants-1996_05
Patent number
US05516777

Reaction notes

Loading…