Hydrochloric Acid → HCID 11574281, compound

HRID 583958Notes

Reaction equation

HRID 583958 reaction equation
[N+:1]([CH:4]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:5][CH2:6][C:7]([O:9]C)=[O:8])([O-:3])=[O:2].[Li+].[OH-].Cl>COCCOC>[N+:1]([CH:4]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:5][CH2:6][C:7]([OH:9])=[O:8])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 15500347HCID 15500347, compound

Product 1

HCID 11574281HCID 11574281, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Methyl 4-nitroheneicosanoate (5a) (147 mg, 0.38 mmol) was dissolved in 1,2-dimethoxyethane (DME) (2 mL) and sat. aq LiOH solution (2 mL) was added. The mixture was left for 24 h, then it was acidified with dilute HCl (10%, 10 mL) and the mixture was extracted with EtOAc (2×10 mL). The extracts were concentrated under a stream of dry N2 and the residue was subjected to flash column chromatography on silica (Et2O/hexane, 100/20, then Et2O/hexane/HOAc, 60/40/1) to afford 4-nitroheneicosanoic acid (6a) (121 mg, 85%) as a white solid; mp 55-56° C.

Workup

  1. extractionthe mixture was extracted with EtOAc (2×10 mL)
  2. concentrationThe extracts were concentrated under a stream of dry N2

Sources & evidence

ORD record
ord-5ef7fb31fbdc4ef1af3eb8214e5b3521
Source dataset
uspto-grants-2005_08
Patent number
US06924309B2

Reaction notes

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