Hydrochloric Acid → 3-(Hexadecyloxy)-2-(tetradecyloxy)propan-1-OL

HRID 1464233

반응식

HRID 1464233 반응식
C(Br)CCCCCCCCCCCCC.[OH-].[K+].C(C(C(CO)O)O)C1C=CC=CC=1.[CH2:31]([O:47][CH2:48][CH:49]([CH2:67][OH:68])[O:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64]CC)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46].C(OCC(COC(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)OCCCCCCCCCCCCCC)CCCCCCCCCCCCCCC.Cl>C1(C)C=CC=CC=1>[CH2:31]([O:47][CH2:48][CH:49]([CH2:67][OH:68])[O:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]

참가 물질

8

반응물 6

HCID 313Hydrochloric AcidHCID 8208Myristyl bromideHCID 14797Potassium HydroxideHCID 1025482,3-Bis(hexadecyloxy)propan-1-olHCID 2735483BenzylglycerolHCID 571290511-Hexadecyl-2-tetradecyl-3-trityl glycerol

생성물 1

HCID 571281113-(Hexadecyloxy)-2-(tetradecyloxy)propan-1-OL

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  1. customA precipitate formed within a short time
  2. filtrationfiltered
  3. customThe solids were recrystallized from acetone (10° C.)

출처 및 근거

ORD 기록
ord-785e311a9d8e436ba22f1c233e6e1851
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05304325

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