Sodium Hydroxide → 3-(4-Methoxy-2-methoxymethoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid

HRID 863157Notes

Reaction equation

HRID 863157 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH2:19][CH2:20][CH3:21])[CH:16]=3)[CH:11]([C:22]3[CH:27]=[CH:26][C:25]4[O:28][CH2:29][O:30][C:24]=4[CH:23]=3)[CH:10]2[C:31]([O:33]C)=[O:32])=[C:5]([O:35][CH2:36][O:37][CH3:38])[CH:4]=1.[OH-].[Na+]>C(O)(C)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH2:19][CH2:20][CH3:21])[CH:16]=3)[CH:11]([C:22]3[CH:27]=[CH:26][C:25]4[O:28][CH2:29][O:30][C:24]=4[CH:23]=3)[CH:10]2[C:31]([OH:33])=[O:32])=[C:5]([O:35][CH2:36][O:37][CH3:38])[CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10142747Methyl (1RS,2SR,3RS)-3-(4-methoxy-2-methoxymethoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylate

Product 1

HCID 187038773-(4-Methoxy-2-methoxymethoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acidYield 85%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of methyl (1RS,2RS,3RS)-3-(4-methoxy-2-methoxymethoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylate (2.42 g, 4.6 mmol) in isopropyl alcohol (30 ml) with aqueous NaOH (8 ml of 5N solution) was refluxed for 4 h. The resultant mixture was partitioned between EtO Ac and 3N HCl. The organic extract was washed with H2O then brine, dried (Na2 SO4) and solvent removed in vacuo to afford the title compound as a colorless oil (1.98 g, 84%).

Workup

  1. customThe resultant mixture was partitioned between EtO Ac and 3N HCl
  2. extractionThe organic extract
  3. washwas washed with H2O
  4. dry with materialbrine, dried (Na2 SO4) and solvent
  5. customremoved in vacuo

Sources & evidence

ORD record
ord-e9b0724a77d349b0936580bf82a7bd24
Source dataset
uspto-grants-1998_02
Patent number
US05719183

Reaction notes

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