Ethylene carbonate → HCID 19004501, compound

HRID 2225717Notes

Reaction equation

HRID 2225717 reaction equation
[O:1]([CH2:8][CH2:9][O:10][C:11]1[C:12]([OH:21])=[CH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(=O)O[CH2:25][CH2:24][O:23]1>[Br-].C([N+](CC)(CC)CC)C.ClCCl>[O:1]([CH2:8][CH2:9][O:10][C:11]1[C:12]([O:21][CH2:25][CH2:24][OH:23])=[CH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 7303Ethylene carbonateHCID 19004539HCID 19004539, compound

Product 1

HCID 19004501HCID 19004501, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 6285Tetraethylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred mixture of 3-(2-phenoxyethoxy)-2-naphthol (3.9 g), ethylene carbonate (1.4 g) and tetraethylammonium bromide (0.8 g) was heated at 155°-160° C. for 2 hours. The cooled reaction was diluted with dichloromethane and washed with 1N sodium hydroxide and with water. The organic layer was dried (Na2SO4), filtered, and evaporated to give crude material which was purified by HPLC (dichloromethane-ethyl acetate; 20:1 ) and crystallized from dichloromethane-diethyl ether to give 3.3 g of 2-[[3-(2-phenoxyethoxy)2-naphthalenyl]oxy]ethanol as a colorless solid, mp 119°-120° C.

Workup

  1. temperaturewas heated at 155°-160° C. for 2 hours
  2. customThe cooled reaction
  3. washwashed with 1N sodium hydroxide and with water
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give crude material which
  8. customwas purified by HPLC (dichloromethane-ethyl acetate; 20:1 )
  9. customcrystallized from dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-a0fd61d555b24c7090fa4f1bf6cf3247
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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