2-Hexyl-1-(2-(phenylmethoxy)-3-(triphenylmethoxy)propoxy)-4-tetradecylbenzene → 3-(2-Hexyl-4-tetradecylphenoxy)-2-(phenylmethoxy)-1-propanol

HRID 34848Notes

Reaction equation

HRID 34848 reaction equation
[CH2:1]([C:7]1[CH:12]=[C:11]([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])[CH:10]=[CH:9][C:8]=1[O:27][CH2:28][CH:29]([O:51][CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[CH2:30][O:31]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]>C(Cl)(Cl)Cl>[CH2:1]([C:7]1[CH:12]=[C:11]([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])[CH:10]=[CH:9][C:8]=1[O:27][CH2:28][CH:29]([O:51][CH2:52][C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1)[CH2:30][OH:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

3

Reactant 1

HCID 150302682-Hexyl-1-(2-(phenylmethoxy)-3-(triphenylmethoxy)propoxy)-4-tetradecylbenzene

Product 1

HCID 142561993-(2-Hexyl-4-tetradecylphenoxy)-2-(phenylmethoxy)-1-propanolYield 70.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 11.9 g of 2-hexyl-1-[2-(phenylmethoxy)-3-(triphenylmethoxy)propoxy]-4-tetradecylbenzene in 250 ml of chloroform was cooled to 0° C. A stream of dry hydrogen chloride gas was bubbled into the solution for 1/2 hour, then the mixture was stirred for 2 hours at 0° C. Solid sodium bicarbonate was added, the mixture stirred for 3 hours, then filtered and the chloroform evaporated. The residue was dissolved in ether, washed with aqueous sodium bicarbonate, dried and the residue chromatographed on silica gel. The column was eluted with hexane:ethyl acetate, giving 5.8 g of the desired compound, mp 32°-33° C.

Workup

  1. customA stream of dry hydrogen chloride gas was bubbled into the solution for 1/2 hour
  2. additionSolid sodium bicarbonate was added
  3. stirringthe mixture stirred for 3 hours
  4. filtrationfiltered
  5. customthe chloroform evaporated
  6. dissolutionThe residue was dissolved in ether
  7. washwashed with aqueous sodium bicarbonate
  8. customdried
  9. customthe residue chromatographed on silica gel
  10. washThe column was eluted with hexane

Sources & evidence

ORD record
ord-a53b35051e6c47a2a657c949b78ed48d
Source dataset
uspto-grants-1988_08
Patent number
US04762942

Reaction notes

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