p-Toluenesulfonic acid → 3-Hydroxymethyl-9-octyloxy-3,8,8,10,10-pentamethyl-9-aza-1,5-dioxaspiro[5.5]undecane

HRID 1900292Notes

Reaction equation

HRID 1900292 reaction equation
[CH2:1]([O:9][N:10]1[C:15]([CH3:17])([CH3:16])[CH2:14][C:13](=[O:18])[CH2:12][C:11]1([CH3:20])[CH3:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH:21][CH2:22][C:23]([CH2:27]O)([CH2:25][OH:26])[CH3:24].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[OH:21][CH2:22][C:23]1([CH3:27])[CH2:25][O:26][C:13]2([CH2:14][C:15]([CH3:17])([CH3:16])[N:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:11]([CH3:19])([CH3:20])[CH2:12]2)[O:18][CH2:24]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6502TrimethylolethaneHCID 22019882N-octyloxy-4-oxo-2,2,6,6-tetramethylpiperidine

Product 1

HCID 233721023-Hydroxymethyl-9-octyloxy-3,8,8,10,10-pentamethyl-9-aza-1,5-dioxaspiro[5.5]undecaneYield 14.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 11.0 grams (38.5 mmol) of 1-octyloxy-2,2,6,6-tetramethylpiperidin-4-one, 10.2 grams (84.9 mmol) of 1,1,1-tris(hydroxymethyl)ethane, 1.4 grams of p-toluenesulfonic acid and 100 ml of toluene is heated at reflux for four hours. Water is collected in a Dean-Stark trap. Purification of the reaction mixture by flash chromatography on silica gel affords 2.1 grams (14% yield) of the title compound as a colorless syrup.

Workup

  1. temperatureis heated
  2. temperatureat reflux for four hours
  3. customWater is collected in a Dean-Stark trap
  4. customPurification of the reaction mixture by flash chromatography on silica gel

Sources & evidence

ORD record
ord-ec25838b1a654643a0849517facef9f2
Source dataset
uspto-grants-1996_11
Patent number
US05574162

Reaction notes

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