p-Toluenesulfonic acid → HCID 15032037, compound

HRID 1761661Notes

Reaction equation

HRID 1761661 reaction equation
[CH3:1][C:2]([CH3:48])([C:39]1[CH:44]=[C:43]([CH2:45][CH3:46])[CH:42]=[CH:41][C:40]=1[OH:47])[CH2:3][N:4]1[C:9](=[O:10])[N:8]([CH2:11][C:12]([C:15]2[CH:20]=[C:19]([CH2:21][CH3:22])[CH:18]=[CH:17][C:16]=2[OH:23])([CH3:14])[CH3:13])[C:7](=[O:24])[N:6]([CH2:25][C:26]([C:29]2[CH:34]=[C:33]([CH2:35][CH3:36])[CH:32]=[CH:31][C:30]=2[OH:37])([CH3:28])[CH3:27])[C:5]1=[O:38].[C:49]1([CH3:59])[CH:54]=CC(S(O)(=O)=O)=C[CH:50]=1.[CH3:60][C:61](=[CH2:63])[CH3:62]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:14][C:12]([CH3:13])([C:15]1[CH:20]=[C:19]([CH2:21][CH3:22])[CH:18]=[C:17]([C:49]([CH3:50])([CH3:54])[CH3:59])[C:16]=1[OH:23])[CH2:11][N:8]1[C:7](=[O:24])[N:6]([CH2:25][C:26]([C:29]2[CH:34]=[C:33]([CH2:35][CH3:36])[CH:32]=[C:31]([C:61]([CH3:62])([CH3:60])[CH3:63])[C:30]=2[OH:37])([CH3:27])[CH3:28])[C:5](=[O:38])[N:4]([CH2:3][C:2]([C:39]2[CH:44]=[C:43]([CH2:45][CH3:46])[CH:42]=[C:41]([C:2]([CH3:39])([CH3:3])[CH3:1])[C:40]=2[OH:47])([CH3:1])[CH3:48])[C:9]1=[O:10]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8255IsobutyleneHCID 15032035HCID 15032035, compound

Product 1

HCID 15032037HCID 15032037, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a 100 ml 3-neck round bottom flask is charged 8.9 g product of Example 4 in 30 ml toluene. To this is added 0.8 g p-toluenesulfonic acid. Isobutylene is passed through the solution while warming to 90° C. When TLC shows the reaction to be complete, the contents are diluted with an equal volume of ethyl acetate and washed 2 times with 50 ml of 5% sodium bicarbonate. The organic layer is dried, and stripped under vacuum. The residue is purified by dry column chromatography to give 3.3 g white solids. Further purification by precipitation from a water/methanol solution gives 2.4 g of product.

Workup

  1. customthe reaction
  2. washwashed 2 times with 50 ml of 5% sodium bicarbonate
  3. customThe organic layer is dried
  4. customThe residue is purified
  5. customby dry column chromatography

Sources & evidence

ORD record
ord-dca021e9cd5c45d89b9e9075d39c4290
Source dataset
uspto-grants-1989_05
Patent number
US04826983

Reaction notes

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