Ethylene Glycol → 2-Hydroxyethyl naphthalene-2-carboxylate

HRID 1486029Notes

Reaction equation

HRID 1486029 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

15.6 g (252 mmol) of ethylene glycol (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.) was dissolved in 100 mL of dehydrated methylene chloride (manufactured by Kanto Chemical Co., Inc.) and 3.49 g (44.0 mmol) of pyridine was added to the solution followed by cooling down with ice water. To this solution, a solution in which 8.00 g (42.0 mmol) of 2-naphthalene carbonyl chloride (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.) was dissolved in 80 mL of methylene chloride was dripped in one hour while being stirred. Subsequent to two hour stirring, the resultant was stirred for six hours at room temperature. The reaction solution was rinsed with water and thereafter the organic phase was isolated followed by drying with magnesium sulfate (manufactured by Kanto Chemical Co., Inc.) and the solvent was distilled away. The remainder was refined by silica gel column chromatography with a solvent mixture of a methylene chloride (manufactured by JUNSEI CHEMICAL CO., LTD.) and methanol (manufactured by Kanto Chemical Co., Inc.) with a volume ratio of 97:3 serving as an eluent to obtain 6.88 g of 2-naphthoic acid 2-hydroxyethyl ester.

Workup

  1. stirringSubsequent to two hour stirring
  2. stirringthe resultant was stirred for six hours at room temperature
  3. washThe reaction solution was rinsed with water
  4. customthe organic phase was isolated
  5. dry with materialby drying with magnesium sulfate (manufactured by Kanto Chemical Co., Inc.)
  6. distillationthe solvent was distilled away
  7. additionThe remainder was refined by silica gel column chromatography with a solvent mixture of a methylene chloride (manufactured by JUNSEI CHEMICAL CO., LTD.) and methanol (manufactured by Kanto Chemical Co., Inc.) with a volume ratio of 97:3 serving as an eluent

Sources & evidence

ORD record
ord-9812dd45bf414e4d83019b9ce9c6601e
Source dataset
uspto-grants-2016_08
Patent number
US09422437B2

Reaction notes

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