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Hydrochloric Acid → 2,5,8,11,14,17,20-Heptaoxadocosan-22-oic acid

HRID 899422
Notes
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Reaction equation

HRID 899422 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][C:22]([O:24]CC)=[O:23].Cl>[OH-].[Na+].[Cl-].[Na+].O>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][C:22]([OH:24])=[O:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11280505Ethyl 2,5,8,11,14,17,20-heptaoxadocosan-22-oate

Product 1

HCID 102916872,5,8,11,14,17,20-Heptaoxadocosan-22-oic acidYield 89.1%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

The product of step (a) (4.54 g) was dissolved in an aqueous sodium hydroxide solution (0.1M) (45 ml) and the reaction was stirred at room temperature for 20 hours. The reaction mixture was acidified to pH 2 by the addition of hydrochloric acid (2M), then this was diluted with brine (300 ml) and extracted with dichloromethane (3×300 ml). The combined organic layers were dried and the solvent removed in vacuo to give the title compound as a yellow oil (3.75 g).

Workup

  1. extractionextracted with dichloromethane (3×300 ml)
  2. customThe combined organic layers were dried
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-4f2a7f2dbea44622ba7afab580bbfb5f
Source dataset
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07354966B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes