Carbon Dioxide → HCID 13454954, compound

HRID 745773Notes

Reaction equation

HRID 745773 reaction equation
Br[C:2]1[C:11]2[C:6](=[C:7]([C:12]([CH3:14])=[CH2:13])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.C([Mg]Br)C.[C:19](=[O:21])=[O:20]>C(OCC)C>[CH3:14][C:12]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[CH:5]=[CH:4][CH:3]=[C:2]2[C:19]([OH:21])=[O:20])=[CH2:13]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 13454953HCID 13454953, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 13454954HCID 13454954, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
20 °C

Procedure

In a nitrogen atmosphere, a solution of 1-bromo-5-(1-methylethenyl)-naphthalene [14.21 g, described by W. F. Short and H. Wang, J. Chem. Soc., 991 (1950)] in diethyl ether (140 ml) was added dropwise to a mixture of ethyl magnesium bromide (prepared from 2.94 g of magnesium and 4.29 ml of ethyl bromide) in diethyl ether (30 ml) at 0° C. The mixture was stirred at 20° C. for 18 hr and then heated at reflux for 1 hr. The cooled solution was poured onto an excess of solid carbon dioxide. The mixture was dissolved in diethyl ether. The resulting solution was washed with a 2N aqueous solution of H2SO4, brine and 10% aqueous NaHCO3 (4x). The basic washes were combined and made acidic (pH 3) with 6N aqueous HCl. The resulting solid was collected, washed with water and dried to give 9.7 g of the title compound; mp 138°-140° C.; NMR(CDCl3) δ 2.15 (s, 3H), 5.0 & 5.38 (2s, 2H), 8.0 (m, 6H), 10.75 (s, 1H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hr
  3. washThe resulting solution was washed with a 2N aqueous solution of H2SO4, brine and 10% aqueous NaHCO3 (4x)
  4. customThe resulting solid was collected
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-315ab5c3b2754b1b9b8300714bb864d4
Source dataset
uspto-grants-1986_07
Patent number
US04600724

Reaction notes

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