Phenol → Isoindoline

HRID 1762470Notes

Reaction equation

HRID 1762470 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-ed6003ffd0734e96b7db47a748fda2b7
Source dataset
uspto-grants-1989_05
Patent number
US04833150

Reaction notes

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