Hydrochloric Acid → HCID 18348588, compound

HRID 2268466Notes

Reaction equation

HRID 2268466 reaction equation
O[CH:2]1[C:10]2[C:5](=[C:6]([O:17][CH3:18])[C:7]([O:15][CH3:16])=[C:8]([O:13][CH3:14])[C:9]=2[O:11][CH3:12])[CH2:4][CH:3]1[CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=1.Cl>[C].[Pd].CO>[CH3:18][O:17][C:6]1[C:7]([O:15][CH3:16])=[C:8]([O:13][CH3:14])[C:9]([O:11][CH3:12])=[C:10]2[C:5]=1[CH2:4][CH:3]([CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=1)[CH2:2]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18348681HCID 18348681, compound

Product 1

HCID 18348588HCID 18348588, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A methanol (30 ml) suspension of methyl 4-[4-(1-hydroxy-4,5,6,7-tetramethoxyindan-2-yl)butoxy]benzoate (1.50 g, 3.26 mmols), concentrated hydrochloric acid (0.0652 ml, 0.652 mmols) and 10% palladium-carbon (300 mg) was stirred under a hydrogen stream at room temperature for 4 hours. The palladium-carbon was removed by filtration, and the filtrate was concentrated in vacuo. The resulting crude product was purified by recrystallization (from hexane) to obtain the entitled compound (1.25 g) as crystals.

Workup

  1. customThe palladium-carbon was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe resulting crude product was purified by recrystallization (from hexane)

Sources & evidence

ORD record
ord-6aa05642f404472c8a4e692abbcd0df0
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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