HCID 68638961, compound → HCID 86595373, compound

HRID 1726825Notes

Reaction equation

HRID 1726825 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([OH:23])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])C1C=CC=CC=1>[Pd].CO>[CH2:9]([OH:8])[CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([OH:23])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 1

HCID 68638961HCID 68638961, compound

Product 1

HCID 86595373HCID 86595373, compoundYield 9.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The resulting compound, 1-benzyloxy-6-tetradecanol (16 g), was hydrogenated overnight using 100 mg of 10% palladium on activated carbon (Degussa AG; Frankfurt, Germany) in 100 ml of methanol to yield 1,6-tetradecandiol (11.1 g, 4.85 mmol). This diol compound, in 100 ml of methylene:pyridine (9:1), was treated with trityl chloride (13.5 g, 4.85 mmol). The mixture was stirred for 4 hours, then washed with ice-cold 10% HCl until the aqueous phase was acidic. Washing in brine then followed this until the aqueous phase was neutral. Solvent removal and chromatography on silica gel in hexane:ethylacetate (80:20) of the oil gave 20.1 g (87%) of the trityl alcohol. The chemical shift of the compound, detected by 1H-NMR, was as follows: 1H-NMR (CDCl3) δ 0.89 (t, 3H, CH3), 1.2-1.7 (m, 22H, CH2), 3.05 (m, 2H, CH2O), 3.55 (m, 1H, CH—O), 3.55 (m, 1H, CH—O), 7.2-7.5 (m, 15H, benzyl).

Sources & evidence

ORD record
ord-88085b98d54441f7be467fb26279508c
Source dataset
uspto-grants-2009_02
Patent number
US07494642B2

Reaction notes

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