p-Toluenesulfonic acid → Methyl 2-(1,3-dioxaindan-5-yl)acetate

HRID 1941263Notes

Reaction equation

HRID 1941263 reaction equation
[CH2:1]1[O:5][C:4]2[CH:6]=[C:7]([CH2:10][C:11]([OH:13])=[O:12])[CH:8]=[CH:9][C:3]=2[O:2]1.[CH3:14]C1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>CO>[CH3:14][O:12][C:11](=[O:13])[CH2:10][C:7]1[CH:8]=[CH:9][C:3]2[O:2][CH2:1][O:5][C:4]=2[CH:6]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 76115Benzo-1,3-dioxole-5-acetic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 266588Methyl 2-(1,3-dioxaindan-5-yl)acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3,4-(methylenedioxy)phenylacetic acid (28.0 g, 155 mmol), catalytic TsOH, and MeOH (125 mL) was stirred over 60 h. Saturated aqueous NaHCO3 was added and the product was extracted into CH2 Cl2. The organic solution was dried (MgSO4), filtered, and concentrated. Distillation (120 -1° C., 1 mmHg) provided the title compound as a clear and colorless oil (27.6 g). 1H NMR (250 MHz, CDCl3): δ6.74 (m, 3H), 5.94 (s, 2H), 3.69 (s, 3H), 3.54 (s, 2H).

Workup

  1. extractionthe product was extracted into CH2 Cl2
  2. dry with materialThe organic solution was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. distillationDistillation (120 -1° C., 1 mmHg)

Sources & evidence

ORD record
ord-3a1fb88a77b34399b4e7d54836b3bd82
Source dataset
uspto-grants-1997_12
Patent number
US05703108

Reaction notes

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