IP Library Patent Application 14000502
Patent Application
App. No. 14/000,502

PROCESS FOR MAKING 2-NITRO-1-ETHANOL DERIVATIVES

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Quick Facts
Patent No.
US None
App. No.
14/000,502
Abstract

A process for making a 2-nitro-1-ethanol derivative of formula III: wherein R3 is as described herein is provided. Novel 2-nitro-1-ethanol derivatives provided.

Claims (14)

1 . A process for making a 2-nitroethanol derivative, the process comprising:

(a) providing a compound of formula I:

wherein R is H or CH 2 OH, and R 1 and R 2 are independently H, C 1 -C 6 alkyl, halo substituted C 1 -C 6 alkyl, aryl, or furanyl;

(b) converting the compound of formula I to a compound of formula II:

wherein R 3 is the residue of an alpha carbon reactant or R 3 is —CH 2 -R 4 wherein R 4 is the residue of an alcohol group reactant;

(c) converting the compound of formula II to a 2-nitroethanol derivative of formula III:

2 . The process of claim 1 wherein R is CH 2 OH and the compound of formula I is prepared by reacting tris(hydroxymethyl)nitromethane with a blocking group precursor.

3 . The process of claim 1 wherein R is H and the compound of formula I is prepared by reacting tris(hydroxymethyl)nitromethane with a blocking group precursor followed by treatment with base to remove a —CH 2 OH group.

4 . The process of claim 2 wherein the blocking group precursor is a geminal diether compound, an aldehyde compound, or a ketone compound.

5 . A compound of formula III-1:

wherein R 5 is C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, aryl, or aralkyl-, wherein cycloalkyl and aryl are optionally substituted with 1 or 2 of C 1 -C 6 alkyl, nitro, halo, alkoxy, or carbonyl.

6 . A compound of formula III-2:

wherein R 6 and R 7 are independently H, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, aryl, or aralkyl-, wherein cycloalkyl and aryl are optionally substituted with 1 or 2 of C 1 -C 6 alkyl, nitro, halo, alkoxy, or carbonyl.

7 - 8 . (canceled)

Assignments (2)
RELEASE OF SECURITY INTEREST Recorded Nov 24, 2020
From: JPMORGAN CHASE BANK, N.A.
To: ANGUS CHEMICAL COMPANY
Reel/Frame 054586/0231 →
SECURITY AGREEMENT Recorded Feb 3, 2015
From: ANGUS CHEMICAL COMPANY
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 034881/0001 →