Diethyl Ether → 2-Propanol, 1-(hexadecyloxy)-3-(triphenylmethoxy)-

HRID 1464232Notes

Reaction equation

HRID 1464232 reaction equation
[CH2:1]([O:17][CH2:18][CH:19]([CH2:21][OH:22])[OH:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:23](Cl)([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(OCC)C>N1C=CC=CC=1>[CH2:1]([O:17][CH2:18][CH:19]([CH2:21][O:22][C:23]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[OH:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6456Trityl chlorideHCID 727331-O-Hexadecylglycerol

Product 1

HCID 4996132-Propanol, 1-(hexadecyloxy)-3-(triphenylmethoxy)-Yield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

1-hexadecyl glycerol (105 g, .33mol) and 93 g (0.33 mol) tritylchloride were dissolved in 300 ml of pyridine. The mixture was heated at 100° C. for 16 hours. After cooling to room temperature 1500 ml of ethyl ether was added and the slurry washed 3 times with cold .5N H2SO4, 5% sodium bicarbonate and 2 times with water. The organic phase was dried over MgSO4, the ether removed on a rotary evaporator and the residue recrystallized from ethanol, yielding the intermediate 1-hexadecyl-3-trityl glycerol (129 g, 70%). The 2 position of this intermediate was alkylated with tetradecyl bromide in the same manner (powdered KOH in toluene) as described earlier for the dialkylation of benzyl glycerol in the preparation of 1,2-dihexadecyl glycerol. The resulting 1-hexadecyl-2-tetradecyl-3-trityl glycerol (128 g) was dissolved in 300 ml of petroleum ether. At room temperature 30 g of anhydrous hydrogen chloride was added. A precipitate formed within a short time. The slurry was stirred at room temperature for 4 hours and then filtered. The solids were recrystallized from acetone (10° C.) to give 45.6 g of product, m.p. 42°-3° C.

Workup

  1. additionwas added
  2. washthe slurry washed 3 times with cold .5N H2SO4, 5% sodium bicarbonate and 2 times with water
  3. dry with materialThe organic phase was dried over MgSO4
  4. customthe ether removed on a rotary evaporator
  5. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-5863802ecc7449359f88f4f9fe34f14b
Source dataset
uspto-grants-1994_04
Patent number
US05304325

Reaction notes

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