p-Toluenesulfonic acid → (+/-)-1-S-hexadecyl-2-O-ethylthioglycerol

HRID 977283Notes

Reaction equation

HRID 977283 reaction equation
[CH2:1]([S:17][CH2:18][CH:19]([CH2:22][OH:23])[O:20][CH3:21])[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].[CH3:24]C(SCC(COC(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)OCC)CCCCCCCCCCCCCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[CH2:1]([S:17][CH2:18][CH:19]([CH2:22][OH:23])[O:20][CH2:21][CH3:24])[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 6101p-Toluenesulfonic acidHCID 145227763-(Hexadecylsulfanyl)-2-methoxypropan-1-olHCID 19965732(+/-)-1-2-hexadecyl-2-O-ethyl-3-O-tritylthioglycerol

Product 1

HCID 14282492(+/-)-1-S-hexadecyl-2-O-ethylthioglycerolYield 95%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

This compound was prepared in an analogous manner to that of (±)-1-S-hexadecyl-2-O-methylthioglycerol from 10.0 grams (0.02 mole) of (±)-1-2-hexadecyl-2-O-ethyl-3-O-tritylthioglycerol and 0.2 gram of p-toluenesulfonic acid. Silica gel chromatography (CHCl3 eluent) provided 5.8 grams (95%) of a semi-waxy solid. 1H-NMR (CDCl3): delta, 0.87(t, 3H, terminal methyl), 1.2-1.6[m, 31H, (CH2)14, CH3 --CH2 --O--], 2.58 (m, 2H, S--CH2), 2.62 (m, 2H, CH--CH2 --S), 3.40-3.50 (m, 3H, CH, CH3 --CH2 --O), 3.75(m, 2H, CH2 --OH).

Sources & evidence

ORD record
ord-6e762c5b93084a23bc549b2276dd7c8f
Source dataset
uspto-grants-1997_03
Patent number
US05614548

Reaction notes

Loading…