Dimethyl Sulfoxide → 2-(Benzyloxy)-3-(hexadecyloxy)propan-1-ol

HRID 1761734Notes

Reaction equation

HRID 1761734 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:27][CH:28](C)[CH:29]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:30][OH:31])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(N(CC)CC)C>C(Cl)Cl.O>[CH2:11]([O:27][CH2:28][CH:29]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:30][OH:31])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 14233170HCID 14233170, compound

Product 1

HCID 132771402-(Benzyloxy)-3-(hexadecyloxy)propan-1-olYield 103.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

A stirred solution of 9.36 g of oxalyl chloride in 130 ml of methylene chloride, under an argon atmosphere was cooled to -70° C. To this was added dropwise 11.53 g of dried dimethyl sulfoxide at a rate to maintain the temperature at -65° to -70° C. After stirring 5 minutes a solution of 10 g of 3-(hexadecyloxy)-2-(phenylmethoxy)-1-butanol in 60 ml of methylene chloride was added dropwise at a fast rate. The pasty mixture was allowed to warm to -10° C. over 20 minutes providing a solution. This solution was recooled to -50° C. and 16.17 g of triethylamine was added dropwise. The reaction mixture was allowed to warm to room temperature and was then poured into 100 ml of water. The organic phase was separated, washed successively with 0.5N hydrochloric acid, saturated aqueous sodium bicarbonate and brine, dried and the solvents removed giving an oil. This oil was dissolved in petroleum ether, washed with water and taken to dryness, giving 10 g of the desired compound as a yellow oil.

Workup

  1. temperatureto maintain the temperature at -65° to -70° C
  2. additionwas added dropwise at a fast rate
  3. customproviding a solution
  4. customwas recooled to -50° C.
  5. temperatureto warm to room temperature
  6. customThe organic phase was separated
  7. washwashed successively with 0.5N hydrochloric acid, saturated aqueous sodium bicarbonate and brine
  8. customdried
  9. customthe solvents removed
  10. customgiving an oil
  11. washwashed with water

Sources & evidence

ORD record
ord-d56cc4d369524381b66f56ab284e8a27
Source dataset
uspto-grants-1989_05
Patent number
US04827011

Reaction notes

Loading…