Ethylene Glycol → 2-Hydroxyethyl naphthalene-2-carboxylate

HRID 1464836Notes

Reaction equation

HRID 1464836 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].N1C=CC=CC=1.[CH:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][C:12]=1[C:21](Cl)=[O:22]>C(Cl)Cl>[OH:3][CH2:2][CH2:1][O:4][C:21]([C:12]1[CH:13]=[CH:14][C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:11]=1)=[O:22]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 1049PyridineHCID 752462-Naphthoyl chloride

Product 1

HCID 713502162-Hydroxyethyl naphthalene-2-carboxylateYield 75.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethylene glycol (15.6 g, 252 mmol) was dissolved in 100 mL of methylene chloride. To this solution, 3.49 g (44 mmol) of pyridine was added and the solution was cooled with ice water. To this solution being stirred, a solution containing 8.00 g (42 mmol) of 2-naphthalenecarbonyl chloride dissolved in 80 mL of methylene chloride was dropped over an hour. This solution was stirred for 2 hours and subsequently further stirred at room temperature for 6 hours. The resultant reaction solution was rinsed with water; the organic phase was then separated and dried over magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography with a methylene chloride/methanol (97/3) solvent mixture serving as an eluent to provide 6.88 g of 2-naphthoic acid 2-hydroxyethyl ester.

Workup

  1. additionwas dropped over an hour
  2. stirringThis solution was stirred for 2 hours
  3. stirringsubsequently further stirred at room temperature for 6 hours
  4. customThe resultant reaction solution
  5. washwas rinsed with water
  6. customthe organic phase was then separated
  7. dry with materialdried over magnesium sulfate
  8. distillationthe solvent was distilled off
  9. customThe residue was purified by silica gel column chromatography with a methylene chloride/methanol (97/3) solvent mixture

Sources & evidence

ORD record
ord-5161a8ec092a415c91d1f5cfd3d86e73
Source dataset
uspto-grants-2015_04
Patent number
US08998400B2

Reaction notes

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