Water → 3-Dodecyloxy-2-decyloxy-1-triphenylmethoxypropane

HRID 964527Notes

Reaction equation

HRID 964527 reaction equation
[CH2:1]([O:13][CH2:14][CH:15]([OH:37])[CH2:16][O:17][C:18]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[H-].[Na+].Br[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50].O>O1CCCC1.C(OCC)C>[CH2:1]([O:13][CH2:14][CH:15]([O:37][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[CH2:16][O:17][C:18]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 81731-BromodecaneHCID 24758Sodium hydrideHCID 159268043-Dodecyloxy-1-triphenylmethoxy-2-propanol

Product 1

HCID 218731963-Dodecyloxy-2-decyloxy-1-triphenylmethoxypropaneYield 52%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Dodecyloxy-1-triphenylmethoxy-2-propanol (13.5 g, 0.027 mol) was added dropwise to an ice-cooled suspension of sodium hydride (80%, 1.6 g, 0.054 mol) in 150 mL of tetrahydrofuran under nitrogen. After stirring for 2 h at room temperature, heat was applied (55° C.). 1-Bromodecane (6 g, 0.027 mol) was added dropwise, and heating continued for 6 h. After cooling for 3 h, water was added slowly. Diethyl ether (2×100 mL) was added, and the solution washed with 15% sodium thiosulfite, water, and brine. After drying over sodium sulfate, the ether was removed, and the residue chromatographed with a gradient of hexanes:ethyl acetate (100:0 to 20:1) to give 9 g (52%) of a clear liquid.

Workup

  1. temperaturecooled
  2. temperatureheat
  3. custom(55° C.)
  4. temperatureheating
  5. waitcontinued for 6 h
  6. temperatureAfter cooling for 3 h
  7. washthe solution washed with 15% sodium thiosulfite, water, and brine
  8. dry with materialAfter drying over sodium sulfate
  9. customthe ether was removed
  10. customthe residue chromatographed with a gradient of hexanes:ethyl acetate (100:0 to 20:1)

Sources & evidence

ORD record
ord-5ac25e0337184591bee0d3084740f077
Source dataset
uspto-grants-1998_06
Patent number
US05770584

Reaction notes

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