Sodium hydride → 1-Tert-butyloxy-2,3-di(2-n-butoxy ethoxy)propane

HRID 865783Notes

Reaction equation

HRID 865783 reaction equation
[C:1]([O:5][CH2:6][CH:7]([OH:10])[CH2:8][OH:9])([CH3:4])([CH3:3])[CH3:2].C(C1C=C(S(OO[CH:24]([CH2:26][CH3:27])[CH3:25])(=O)=O)C=CC=1C)C.[H-].[Na+]>>[C:1]([O:5][CH2:6][CH:7]([O:10][CH2:7][CH2:8][O:9][CH2:27][CH2:26][CH2:24][CH3:25])[CH2:8][O:9][CH2:2][CH2:1][O:5][CH2:25][CH2:24][CH2:26][CH3:27])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 52284683-Tert-butoxy-1,2-propanediolHCID 867499482-n-Butoxy ethyl-toluene-p-sulfonate

Product 1

HCID 233746721-Tert-butyloxy-2,3-di(2-n-butoxy ethoxy)propane

Procedure

Compound 25 was prepared using a method similar to that described for 23. The o reagents used were as follows, compound 17 (25.5 g, 0.172 mol.), compound 19 (91.5 g, 0.336 mol.), sodium hydride (60% by wt. in mineral oil (14.0 g, 0.350 mol.). The final product was a colorless liquid (30.0 g 60%) (bpt. 100°-120 0° C., 0.06 torr.): 1H-NMR (CDCl3), d (ppm) 3.8-3.4 (m, 17H), 1.55 (m, 4H, CH2), 1.2 (s, 9H, C(CH3)3), 0.9 (t, 6H, --CH3). Mass spectroscopy, m/e 349 MH+.

Workup

  1. customCompound 25 was prepared
  2. customa colorless liquid (30.0 g 60%) (bpt. 100°-120 0° C., 0.06 torr.)

Sources & evidence

ORD record
ord-08a380345d24400798d6e460420dd3bb
Source dataset
uspto-grants-1996_10
Patent number
US05567783

Reaction notes

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