Hydrochloric Acid → HCID 18348607, compound

HRID 2268504Notes

Reaction equation

HRID 2268504 reaction equation
Br[C:2]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[C:8]([O:15][CH3:16])=[C:7]2[C:3]=1[CH2:4][CH:5]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]1[CH2:31][C:30]3[C:25](=[C:26]([O:37][CH3:38])[C:27]([O:35][CH3:36])=[C:28]([O:33][CH3:34])[C:29]=3Br)[CH2:24]1)[CH2:6]2.[C:39](OCC)(=[O:41])C.[CH3:45][O-:46].[Na+].Cl>O>[CH3:39][O:41][C:2]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[C:8]([O:15][CH3:16])=[C:7]2[C:3]=1[CH2:4][CH:5]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]1[CH2:31][C:30]3[C:25](=[C:26]([O:37][CH3:38])[C:27]([O:35][CH3:36])=[C:28]([O:33][CH3:34])[C:29]=3[O:46][CH3:45])[CH2:24]1)[CH2:6]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 18348539HCID 18348539, compound

Product 1

HCID 18348607HCID 18348607, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1,6-bis(4-bromo-5,6,7-trimethoxyindan-2-yl)hexane (2.10 g), copper bromide(I) (230 mg), ethyl acetate (0.625 ml), and sodium methoxide (28% methanol solution; 100 ml) was heated under reflux for 12 hr. Water was added to the reaction mixture, which was made acidic with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium chloride, and dried. The solvent was removed in vacuo. The residue was purified by alumina column chromatography (hexane to hexane:ethyl acetate=8:1) to yield the entitled compound (1.22 g) as crystals.

Workup

  1. temperatureunder reflux for 12 hr
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water, saturated aqueous sodium chloride
  4. customdried
  5. customThe solvent was removed in vacuo
  6. customThe residue was purified by alumina column chromatography (hexane to hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-abbe76716d264918b78b9fe93533abb3
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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