Hydrochloric Acid → HCID 18348557, compound

HRID 2268468Notes

Reaction equation

HRID 2268468 reaction equation
[OH-].[Na+].CO.[CH3:5][O:6][C:7]1[C:15]([O:16][CH3:17])=[C:14]([O:18][CH3:19])[C:13]([O:20][CH3:21])=[C:12]2[C:8]=1[CH2:9][CH:10]([CH2:22][CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:36]=[CH:35][C:30]([C:31]([O:33]C)=[O:32])=[CH:29][CH:28]=1)[CH2:11]2.Cl>O>[CH3:21][O:20][C:13]1[C:14]([O:18][CH3:19])=[C:15]([O:16][CH3:17])[C:7]([O:6][CH3:5])=[C:8]2[C:12]=1[CH2:11][CH:10]([CH2:22][CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:36]=[CH:35][C:30]([C:31]([OH:33])=[O:32])=[CH:29][CH:28]=1)[CH2:9]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 18348588HCID 18348588, compound

Product 1

HCID 18348557HCID 18348557, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An aqueous sodium hydroxide solution (3 N, 1.04 ml, 3.12 mmols) was added to a methanol (10 ml) solution of methyl 4-[4-(4,5,6,7-tetramethoxyindan-2-yl)butoxy]benzoate (920 mg, 2.07 mmols), and heated under reflux for 6 hours. Water was added to the reaction mixture, which was made acidic by adding 1 N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out in vacuo, and the resulting crude product was purified by recrystallization (from hexane-ethyl acetate) to obtain the entitled compound (855 mg) as crystals.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 6 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. customdried
  6. customThe solvent was evaporated out in vacuo
  7. customthe resulting crude product was purified by recrystallization (from hexane-ethyl acetate)

Sources & evidence

ORD record
ord-247bd63d803a4bbba47c8c6142b80207
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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