Toluene → HCID 19876841, compound

HRID 1886093Notes

Reaction equation

HRID 1886093 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH:11]1[CH2:19][C:18]2[C:13](=[CH:14][C:15]([O:20]C)=[CH:16][CH:17]=2)[C:12]1=[O:22])([OH:3])=[O:2].[Al+3].[Cl-].[Cl-].[Cl-].[NH4+].[Cl-].[C:29]1(C)C=CC=CC=1>>[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH:11]1[CH2:19][C:18]2[C:13](=[CH:14][C:15]([OH:20])=[CH:16][CH:17]=2)[C:12]1=[O:22])([O:3][CH3:29])=[O:2]

Participants

5

Reactant 4

HCID 1140TolueneHCID 25517Ammonium ChlorideHCID 6451240Aluminum(III) ChlorideHCID 19876839HCID 19876839, compound

Product 1

HCID 19876841HCID 19876841, compoundYield 70%

Conditions

Temperature
60 °C

Procedure

To a solution of the product of Step 2 (25 g, 84.5 mmol) in toluene (1.2 L) at 60° C. was added AlCl3 (45 g, 338 mmol) in portions. The mixture was stirred at 60° C. for 14 hrs. NH4Cl solution was added and the mixture was extracted with EtOAc. The crude concentrated extract was treated with excess CH2N2 in Et2O. Chromatography of the resulting product on silica gel (eluted with 30% EtOAc/hexane) gave 17.5 g (70%) of the title compound.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. concentrationThe crude concentrated
  3. extractionextract
  4. additionwas treated with excess CH2N2 in Et2O

Sources & evidence

ORD record
ord-990baa7adabb42c9892d0b0d7fb91092
Source dataset
uspto-grants-1992_09
Patent number
US05149703

Reaction notes

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