Ethylene Glycol → HCID 22624491, compound

HRID 279079Notes

Reaction equation

HRID 279079 reaction equation
[OH-].[K+].C(O)CO.[OH:7][C:8]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[O:39][CH2:40][CH2:41][O:42]C(=O)C)[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:17]([O:19]C)=[O:18])[CH2:10][CH2:9]1.Cl>O>[OH:7][C:8]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[O:39][CH2:40][CH2:41][OH:42])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:17]([OH:19])=[O:18])[CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 22624495HCID 22624495, compound

Product 1

HCID 22624491HCID 22624491, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

In a mixture of 4 mL of a 25% aqueous solution of potassium hydroxide and 5 mL of ethylene glycol was dissolved 350 mg (0.66 mmol) of methyl 4-(4-hydroxy-4-(2-(2-acetoxyethoxy)phenyl)piperidino)-2,2-diphenylbutyrate. The resulting solution was stirred at 130° C. for 2 hours. Water was added to the reaction mixture, followed by neutralization with hydrochloric acid under ice cooling. The crystals thus precipitated were collected by filtration and dried, whereby 230 mg (yield: 73.4%) of 4-(4-hydroxy-4-(2-(2-hydroxyethoxy)phenyl)piperidino)-2,2-diphenylbutyric acid was obtained.

Workup

  1. customThe crystals thus precipitated
  2. filtrationwere collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-8f9fee2212b84ab9a572cb2eecd31e2b
Source dataset
uspto-grants-2002_03
Patent number
US06362203B1

Reaction notes

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