Sulfamic Acid → 4-Methoxy-indan-5-carboxylic acid

HRID 1099375Notes

Reaction equation

HRID 1099375 reaction equation
[CH3:1][O:2][C:3]1[C:11]([CH:12]=[O:13])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][CH2:7]2.S(=O)(=O)([OH:16])N.Cl([O-])=O.[Na+]>ClCCl.O>[CH3:1][O:2][C:3]1[C:11]([C:12]([OH:16])=[O:13])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][CH2:7]2

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 23668197Sodium ChloriteHCID 866431044-Methoxy-indan-5-carbaldehyde

Product 1

HCID 668121244-Methoxy-indan-5-carboxylic acidYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
26.5 °C

Procedure

To a clear solution of 4-Methoxy-indan-5-carbaldehyde (11.5 gm, 0.065 mole) in Dichloromethane (100 ml), Sulphamic acid (19.0 gm, 0.196 mole) was added at 25-28°. A solution of Sodium chlorite (15.28 gm, 0.169 mole) in water (50 ml) was added at 5-10° C. The reaction mixture was stirred for 5 hours at 25-28° C. Finally the reaction mixture was poured into water (200 ml) and extracted with Dichloromethane (2×200 ml). The organic layer was dried over Sodium sulphate, distilled under vacuum to give 12.0 gm of desired product as a viscous oil.

Workup

  1. extractionextracted with Dichloromethane (2×200 ml)
  2. dry with materialThe organic layer was dried over Sodium sulphate
  3. distillationdistilled under vacuum

Sources & evidence

ORD record
ord-891f72291788451aa671417d99a8b58a
Source dataset
uspto-grants-2012_03
Patent number
US08143424B2

Reaction notes

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