Triethylene Glycol → HCID 53897125, compound

HRID 2225706Notes

Reaction equation

HRID 2225706 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:25])[C:22]([OH:24])=[O:23])=[CH:17][CH:16]=1.[CH2:26]([OH:35])[CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33]O>ClCCl>[OH:35][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:23][C:22](=[O:24])[C:21](=[O:25])[C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][CH2:12][O:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 8172Triethylene GlycolHCID 19004267HCID 19004267, compound

Product 1

HCID 53897125HCID 53897125, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The acid chloride, prepared from 4-[[2-(2-naphthalenyloxy)ethyl]oxy]-alpha-oxobenzene-acetic acid (0.5 g) as described in Example 6, was dissolved in dichloromethane (10 mL) and added dropwise to a stirred, cold (<-50° C.) mixture of triethylene glycol (0.9 g) in dichloro-methane (10 mL). The cooling bath was removed and the mixture stirred for 1 hour at room temperature. The mixture was diluted with dichloromethane and washed once with saturated aqueous sodium bicarbonate, once with water, and the organic solution was dried (Na2SO4), filtered, and evaporated to give crude product. The material was purified by HPLC (dichloro-methane-ethyl acetate; 2:1) to provide, after crystallization from ethyl acetate-hexane, 0.36 g of 4-[[2-(2-naphthalenyloxy)ethyl]oxy]-alpha-oxobenzeneacetic acid 2-[2-(2-hydroxyethoxy)ethoxy]ethyl ester as a colorless solid, mp 70°-71° C.

Workup

  1. customThe cooling bath was removed
  2. additionThe mixture was diluted with dichloromethane
  3. washwashed once with saturated aqueous sodium bicarbonate, once with water
  4. dry with materialthe organic solution was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give crude product
  8. customThe material was purified by HPLC (dichloro-methane-ethyl acetate; 2:1)
  9. customto provide
  10. customafter crystallization from ethyl acetate-hexane, 0.36 g of 4-[[2-(2-naphthalenyloxy)ethyl]oxy]-alpha-oxobenzeneacetic acid 2-[2-(2-hydroxyethoxy)ethoxy]ethyl ester as a colorless solid, mp 70°-71° C.

Sources & evidence

ORD record
ord-093eea8ce8564cf3ada812be7e90d553
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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