6-Nitroveratryl alcohol → 4,5-Dimethoxy-2-nitrobenzyl hexadecanesulfonate

HRID 745714

Reaction equation

HRID 745714 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][C:6]([CH2:7][OH:8])=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=1.[CH2:16]([S:32](Cl)(=[O:34])=[O:33])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>CC(C)=O.C1(NC2CCCCC2)CCCCC1>[CH2:16]([S:32]([O:8][CH2:7][C:6]1[CH:9]=[C:10]([O:11][CH3:12])[C:3]([O:2][CH3:1])=[CH:4][C:5]=1[N+:13]([O-:15])=[O:14])(=[O:34])=[O:33])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 2

HCID 660976-Nitroveratryl alcoholHCID 969231-Hexadecanesulfonyl chloride

Product 1

HCID 537926464,5-Dimethoxy-2-nitrobenzyl hexadecanesulfonate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 7582DicyclohexylamineSolvent

Procedure

To a solution of 5.33 g (0.025 mol) of 4,5-dimethoxy-2-nitrobenzyl alcohol and 8.15 g (0.025 mol) hexadecanesulfonyl chloride in 100 ml of acetone, dicyclohexylamine (5 ml, slight excess) was added via motor driven syringe over 30 minutes. After the addition was complete, the reaction was stirred an additional 30 minutes. The precipitated dicyclohexylamine hydrochloride was removed by filtration and the acetone filtrate reduced in volume in vacuo until most of the product had precipitated (yield 9.5 g, m.p. 81°-82° C.).

Workup

  1. customover 30 minutes
  2. additionAfter the addition
  3. customThe precipitated dicyclohexylamine hydrochloride was removed by filtration
  4. customhad precipitated (yield 9.5 g, m.p. 81°-82° C.)

Sources & evidence

ORD record
ord-9e924dbf4a46448bbd2294eb5b08842e
Source dataset
uspto-grants-1986_07
Patent number
US04599273

Linked notes

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