6-Dodecyl-6-(2-hydroxybenzyl)-13,13-dimethyl-1,4,8,11-tetraoxacyclotetradecane → HCID 135727116, compound

HRID 5539Notes

Reaction equation

HRID 5539 reaction equation
[CH2:1]([C:13]1([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[OH:36])[CH2:26][O:25][CH2:24][CH2:23][O:22][CH2:21][C:20]([CH3:28])([CH3:27])[CH2:19][O:18][CH2:17][CH2:16][O:15][CH2:14]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].F[P-](F)(F)(F)(F)F.[CH3:44][S:45]([C:48]1[CH:53]=[C:52]([N+:54]([O-:56])=[O:55])[CH:51]=[CH:50][C:49]=1[N+:57]#[N:58])(=[O:47])=[O:46]>C(O)(=O)C.O.O1CCCC1>[CH2:1]([C:13]1([CH2:29][C:30]2[CH:35]=[C:34]([N:58]=[N:57][C:49]3[CH:50]=[CH:51][C:52]([N+:54]([O-:56])=[O:55])=[CH:53][C:48]=3[S:45]([CH3:44])(=[O:47])=[O:46])[CH:33]=[CH:32][C:31]=2[OH:36])[CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][C:20]([CH3:27])([CH3:28])[CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 2

HCID 156518386-Dodecyl-6-(2-hydroxybenzyl)-13,13-dimethyl-1,4,8,11-tetraoxacyclotetradecaneHCID 197961922-Methylsulfonyl-4-nitrophenyldiazonium hexafluorophosphate

Product 1

HCID 135727116HCID 135727116, compoundYield 4.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.1 g (6.1 mmol) of Compound 15 in 50 cc acetic acid at 5° C. was added a solution of 3.0 g (8.0 mmol) of 2-methylsulfonyl-4-nitrophenyldiazonium hexafluorophosphate in 25 cc water and 75 cc tetrahydrofuran. The suspension was stirred at room temperature for 16 hours. The product was extracted into ethyl acetate and isolated by silica gel chromatography yielding 0.22 g (4.7%) of Compound 16. The 1H NMR spectrum is consistent with the assigned structure.

Workup

  1. extractionThe product was extracted into ethyl acetate
  2. customisolated by silica gel chromatography

Sources & evidence

ORD record
ord-6d9cce36bc1640beacc29f308680a163
Source dataset
uspto-grants-1993_09
Patent number
US05245021

Reaction notes

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