Hydrochloric Acid → HCID 14832881, compound

HRID 2165984Notes

Reaction equation

HRID 2165984 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].CCO[CH2:14][CH3:15].Br[C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[C:23]([C:27]1[C:36]3[C:31](=[CH:32][C:33](Br)=[CH:34][CH:35]=3)[CH:30]=[CH:29][C:28]=1[O:38][CH3:39])=[C:22]([O:40][CH3:41])[CH:21]=[CH:20]2.Cl>ClCCl>[CH2:1]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[C:23]([C:27]1[C:36]3[C:31](=[CH:32][C:33]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:14][CH3:15])=[CH:34][CH:35]=3)[CH:30]=[CH:29][C:28]=1[O:38][CH3:39])=[C:22]([O:40][CH3:41])[CH:21]=[CH:20]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 27940731,1'-Binaphthalene, 6,6'-dibromo-2,2'-dimethoxy-HCID 178443577HCID 178443577, compound

Product 1

HCID 14832881HCID 14832881, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

63 mmol (100 ml of ether solution) of C8H17MgBr were added in a nitrogen atmosphere to a ether solution (150 ml) containing 10 g of Compound 1 and 1.25 g of dichloro[1,3-bis(diphenylphosphine)propane]nickel, and refluxed for 20 hours. After cooling down, 800 ml each of dichloromethane and 1M hydrochloric acid were added to obtain an oily reaction product by extraction. By purifying the above reaction product with column chromatography (silica gel, petroleum ether/ethyl ether), 8.1 g of pure 6,6'-dioctyl-2,2'-dimethoxy-1,1'-binaphthyl (Compound 2) were obtained (yield: 72%).

Workup

  1. temperaturerefluxed for 20 hours
  2. temperatureAfter cooling down
  3. customto obtain an oily reaction product
  4. extractionby extraction
  5. customBy purifying the above reaction product with column chromatography (silica gel, petroleum ether/ethyl ether)

Sources & evidence

ORD record
ord-d128bfeb00034216a1d26c3fa760a2c9
Source dataset
uspto-grants-1990_07
Patent number
US04942149

Reaction notes

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