Formaldehyde → 1-(Methoxymethyl)-2-pyrrolidinone

HRID 1076194Notes

Reaction equation

HRID 1076194 reaction equation
[OH:1][CH2:2][N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8].N1CCC[C:10]1=O.C=O.ClCN1CCCC1=O.C[O-].[Na+]>CO>[CH3:10][O:1][CH2:2][N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8]

Participants

7

Reactant 5

HCID 712Formaldehyde2×HCID 120252-PyrrolidoneHCID 849112-Pyrrolidinone, 1-(hydroxymethyl)-HCID 27704972-Pyrrolidinone, 1-(chloromethyl)-HCID 10942334Sodium Methoxide

Product 1

HCID 136248301-(Methoxymethyl)-2-pyrrolidinoneYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-hydroxymethyl pyrrolidinone is a compound known in the art as an intermediate in the preparation of dyestuffs. As taught in U.S. Pat. No. 3,073,843, this material is prepared by the reaction of pyrrolidinone and formaldehyde or a precursor of formaldehyde. This patent does not suggest the formation of derivatives of this compound however. In addition, Chemical Abstracts, Volume 55, page 27267H (1961) discloses the reaction of N-chloromethyl-2-pyrrolidinone with a mixture of sodium methylate and methanol to yield 64% of N-methoxymethyl-2-pyrrolidinone. Also, Chemical Abstracts, Volume 54, page 1286f (1960) teaches that N-chloromethyl-2-pyrrolidinone can be prepared in 87% yield by treatment of the methylol derivative with SOCl2 in benzene solvent at 8°C.

Workup

  1. customknown in the art as an intermediate in the preparation of dyestuffs

Sources & evidence

ORD record
ord-111e7a6cc2cf4bf6b7b416acecfbb6b7
Source dataset
uspto-grants-1976_05
Patent number
US03956313

Reaction notes

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