Hydrogen Peroxide → 3-Hexadecyloxy-2-triphenylmethoxymethylpropan-1-ol

HRID 34299Notes

Reaction equation

HRID 34299 reaction equation
C(OC([CH2:21][O:22][C:23]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)C=C)CCCCCCCCCCCCCCC.[OH2:42].[OH-].[Na+].OO.[O:47]1[CH2:51][CH2:50][CH2:49][CH2:48]1>O1CCOCC1>[CH2:51]([O:47][CH2:37][CH:36]([CH2:21][O:22][C:23]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:41][OH:42])[CH2:50][CH2:49][CH2:48][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 962WaterHCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21299166HCID 21299166, compound

Product 1

HCID 212991503-Hexadecyloxy-2-triphenylmethoxymethylpropan-1-olYield 66%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of compound 2 (5.00 g, 9.01 mmol) in 10 ml dry dioxane and BH3 -tetrahydrofuran (10 ml, 10.0 mmol) in tetrahydrofuran was stirred at room temperature for 2 hours. Water (10 ml) was added dropwise, followed by 2.5 N NaOH (20 ml) and 30% H2O2 (7.5 ml). The mixture was stirred at 50° for 2.5 hours, then was cooled and partitioned between CH2Cl2 and water. The aqueous layer was washed 3 times with CH2Cl2 and the combined extracts were dried over Na2SO4 and concentrated. Chromatography on silica gel using 10% ethyl acetatehexane afforded 3.37 g (66%) of the title compound (4) as a waxy white solid, m.p. 38°. NMR (CDCl3, (CH3)4Si); δ0.90 (t, 3H, J=6 Hz, --CH3), 1.25 (s, 26 H, --CH2 --), 1.54 (m, 2H, --OCH2CH2R), 2.16 (m, 1H, CH), 2.70 (t, 1H, J=6.5 Hz, --OH), 3.22 (d, 2H, J=6 Hz, CH2OTr), 3.41 (t, 2H, J=6 Hz, --OCH2R), 3.61 (t, 2H, J=6 Hz, CH2OR), 3.77 (t, 2H, J=6.5 Hz, CH2OH), 7.2-7.52 (m, 15H, C(C6H5)3).

Workup

  1. temperaturewas cooled
  2. custompartitioned between CH2Cl2 and water
  3. washThe aqueous layer was washed 3 times with CH2Cl2
  4. dry with materialthe combined extracts were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8cf99d7e543a46e49c1fad7ea73c3f9e
Source dataset
uspto-grants-1988_08
Patent number
US04761404

Reaction notes

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