Dichloromethane → 1-(12-Cyclohexyldodecyloxy)-3-trityloxy-2-propanol

HRID 478100Notes

Reaction equation

HRID 478100 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH:21]([CH2:23][OH:24])[OH:22])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:25](Cl)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C.ClCCl>CO>[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH:21]([CH2:23][O:24][C:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[OH:22])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 148777223-[(12-Cyclohexyldodecyl)oxy]propane-1,2-diol

Product 1

HCID 148777231-(12-Cyclohexyldodecyloxy)-3-trityloxy-2-propanolYield 129.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 23.5 g (68.6 millimole) of 1-O-(12-cyclohexyl)dodecylglycerol, 28.7 g (103 millimole) of trityl chloride, 13.7 g (137 millimole) of triethylamine and 200 ml of dichloromethane was stirred at room temperature for 2 days, and to the reaction mixture was added 10 ml of methanol. The resulting mixture was further stirred for 3 hours, and washed with water and dried (MgSO4), followed by evaporation of the solvents, to give 52 g (quantitative) of crude 1-O-(12-cyclohexyl)dodecyl-3-O-tritylglycerol.

Workup

  1. stirringThe resulting mixture was further stirred for 3 hours
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. customfollowed by evaporation of the solvents

Sources & evidence

ORD record
ord-8f5e376f32814faeb4bb6924563ff5b0
Source dataset
uspto-grants-1989_12
Patent number
US04889953

Reaction notes

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