Acetic Acid → 1-(3,4,5-Trimethoxyphenyl)-2-nitro-1,3-propanediol

HRID 2417621Notes

Reaction equation

HRID 2417621 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH:6]=[O:7].[N+:15]([CH:18](O)[CH3:19])([O-:17])=[O:16].C(Cl)(Cl)Cl.C(O)(=[O:27])C>CO.CN1CCCCC1>[CH3:14][O:13][C:9]1[CH:8]=[C:5]([CH:6]([OH:7])[CH:18]([N+:15]([O-:17])=[O:16])[CH2:19][OH:27])[CH:4]=[C:3]([O:2][CH3:1])[C:10]=1[O:11][CH3:12]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6212ChloroformHCID 68583,4,5-TrimethoxybenzaldehydeHCID 22056827Nitroethanol

Product 1

HCID 134688871-(3,4,5-Trimethoxyphenyl)-2-nitro-1,3-propanediol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 12291N-MethylpiperidineSolvent

Procedure

19.6 g (0.1 moles) of 3,4,5-trimethoxybenzaldehyde and 9.1 g (0.1 moles) of nitroethanol are suspended in a mixture of 25 ml of methanol and 1 ml of N-methylpiperidine at a temperature of 0° C. (under cooling with ice water). The reaction mixture is stirred for 6 hours, then 50 ml of chloroform are added, the mixture is allowed to stand at 0° C. for 72 hours and then acidified with 1 ml of acetic acid. The separated crystalline substance is filtered off, washed with chloroform and ice-cold (0° C.) water and dried. 19.7 g 68.64%) of 1-(3,4,5-trimethoxyphenyl)-2-nitro-1,3-propanediol are obtained; m.p.: 155°-159° C.

Workup

  1. waitto stand at 0° C. for 72 hours
  2. filtrationThe separated crystalline substance is filtered off
  3. washwashed with chloroform and ice-cold (0° C.) water
  4. customdried

Sources & evidence

ORD record
ord-5802cf88c82f4a039286fd237ccba50f
Source dataset
uspto-grants-1984_09
Patent number
US04469703

Reaction notes

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