Sodium Hydroxide → 5,7-Dimethoxy-indan-1-one

HRID 2100745Notes

Reaction equation

HRID 2100745 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]([OH:15])=O)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[OH-].[Na+]>CS(O)(=O)=O>[CH3:10][O:9][C:7]1[CH:6]=[C:5]2[C:4](=[C:3]([O:2][CH3:1])[CH:8]=1)[C:13](=[O:15])[CH2:12][CH2:11]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 38702163-(3,5-dimethoxyphenyl)propanoic Acid

Product 1

HCID 43702075,7-Dimethoxy-indan-1-oneYield 481.2%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
90 °C

Procedure

The 3-(3,5-Dimethoxy-phenyl)-propionic acid (2 g×5) was dissolved in methanesulfonic acid (10 ml×5) in microwave process vial (20 ml×5), the mixture was heated at 90° C. for 10 minutes under microwave irradiation. The mixture was poured into ice (250 g), neutralized by 2M NaOH to PH 8-9, and extracted by EtOAc. The organic layer was concentrated to give the product (8.8 g, 96.2%). LC-MS: m/e 193 (MH+)

Workup

  1. extractionextracted by EtOAc
  2. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-1d68c84180a141399e91d108d6d7e976
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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