Methanol → 3-(3-Oxo-6-pentyloxyindan-5-yloxymethyl)benzoic Acid

HRID 242449Notes

Reaction equation

HRID 242449 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[C:8]([O:11][CH2:12][C:13]3[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=3)[C:16]([O:18]C)=[O:17])[CH:9]=2)[CH2:4][CH2:3]1.CO.[OH-].[Na+].O>C(Cl)Cl>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[C:8]([O:11][CH2:12][C:13]3[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=3)[C:16]([OH:18])=[O:17])[CH:9]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 57458787Methyl 3-(3-oxo-6-pentyloxyindan-5-yloxymethyl)benzoate

Product 1

HCID 115451513-(3-Oxo-6-pentyloxyindan-5-yloxymethyl)benzoic AcidYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of the compound obtained in Example 3 (2.3 g; 6.01 mmol), methanol (330 ml), sodium hydroxide (0.96 g; 24 mmol) and water (24 ml) is refluxed for 3 hours. The medium is concentrated to dryness. The residue is taken up in water. The basic aqueous phase is washed with ethyl ether and then acidified with 1N HCl. The cream-coloured precipitate formed is dissolved in methylene chloride. The organic phase is washed with water, dried over sodium sulfate and concentrated (1.5 g; 68% yield).

Workup

  1. temperatureis refluxed for 3 hours
  2. concentrationThe medium is concentrated to dryness
  3. washThe basic aqueous phase is washed with ethyl ether
  4. customThe cream-coloured precipitate formed
  5. washThe organic phase is washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated (1.5 g; 68% yield)

Sources & evidence

ORD record
ord-a24612d7197d4e4d887ccd35f0461825
Source dataset
uspto-grants-2014_02
Patent number
US08653134B2

Reaction notes

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