Phenol → Isoindoline

HRID 1906478Notes

Reaction equation

HRID 1906478 reaction equation
C1(C)C=CC(S([N:10]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11]2)(=O)=O)=CC=1.C1(O)C=CC=CC=1.C(O)(=O)CC>Br>[CH2:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:18][NH:10]1

Participants

5

Reactant 3

HCID 996PhenolHCID 1032Propionic AcidHCID 2598992-Tosylisoindoline

Product 1

HCID 422478IsoindolineYield 62.6%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 12.0 g (0.044 mol) of 2-(p-tolylsulfonyl) isoindoline, 12.0 g (0.13 mol) of phenol, 90 ml of 48% HBr, and 15 ml (0.201 mol) of propionic acid was refluxed for two hours. The mixture was cooled to room temperature, triturated with diethyl ether, and then added to a solution of 75 gm of sodium hydroxide in 200 ml of cold water. This mixture was extracted with diethyl ether and the combined ether extracts were washed with water. The organic phase was dried over magnesium sulfate, concentrated in vacuo and kugelrohr distilled to give 3.28 g (61%) of a white solid, m.p. 118°-127° C. NMR: (CDCl3) δ 2.2 (1H,s), 4.0 (4H, s), 6.95 (4H, s)

Workup

  1. customtriturated with diethyl ether
  2. additionadded to a solution of 75 gm of sodium hydroxide in 200 ml of cold water
  3. extractionThis mixture was extracted with diethyl ether
  4. washthe combined ether extracts were washed with water
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. concentrationconcentrated in vacuo and kugelrohr
  7. distillationdistilled

Sources & evidence

ORD record
ord-72b59f4b8c094f22a89f22d39068a8b4
Source dataset
uspto-grants-1987_03
Patent number
US04652573

Reaction notes

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