Hydrochloric Acid → 2-(p-Nitrophenoxy)-myristic acid

HRID 620702Notes

Reaction equation

HRID 620702 reaction equation
C([O:3][C:4](=[O:28])[CH:5]([O:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])C.C(OC(=O)C(OC1C=CC=C([N+]([O-])=O)C=1)CCCCCCCCCCCC)C.[OH-].[Na+].Cl>C(O)C>[N+:25]([C:22]1[CH:21]=[CH:20][C:19]([O:18][CH:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:4]([OH:28])=[O:3])=[CH:24][CH:23]=1)([O-:27])=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14122414Ethyl 2-(3-nitrophenoxy)tetradecanoateHCID 54095639Ethyl 2-(4-nitrophenoxy)tetradecanoate

Product 1

HCID 37465002-(p-Nitrophenoxy)-myristic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 980 g of 2-(p-nitrophenoxy)-myristic acid ethyl ester (synthesized analogously to the 2-(m-nitrophenoxy)-myristic acid ethyl ester of Preparation 1), 375 ml of 10N sodium hydroxide, and 1500 ml of ethanol is stirred for 1 h at room temperature and next acidified with 5000 ml of 1N hydrochloric acid. The resulting precipitate is filtered off, rinsed with water until neutral, and dried. The product (845 g) was recrystallized from n-hexane.

Workup

  1. filtrationThe resulting precipitate is filtered off
  2. washrinsed with water until neutral, and
  3. customdried
  4. customThe product (845 g) was recrystallized from n-hexane

Sources & evidence

ORD record
ord-a866a4cb93004cd1b249373b89c0efd7
Source dataset
uspto-grants-1989_04
Patent number
US04822729

Reaction notes

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