Methanol → 3-Dodecyloxy-2-decyloxy-1-propanol

HRID 964528Notes

Reaction equation

HRID 964528 reaction equation
[CH2:1]([O:13][CH2:14][CH:15]([O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:16][O:17]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C1(C)C=CC(S(O)(=O)=O)=CC=1.CO>C(Cl)(Cl)Cl>[CH2:1]([O:13][CH2:14][CH:15]([O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:16][OH:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 218731963-Dodecyloxy-2-decyloxy-1-triphenylmethoxypropane

Product 1

HCID 150778443-Dodecyloxy-2-decyloxy-1-propanolYield 63%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Detritylation of 3-dodecyloxy-2-decyloxy-1 -triphenylmethoxypropane was accomplished using p-toluenesulfonic acid (0.9 g) in CHCl3 :MeOH (72 mL:36 mL) (stirred at room temperature for 48 h, added 10% sodium bicarbonate, extracted with CHCl3, dried over magnesium sulfate, and concentrated). The residue was purified by column chromatography using a gradient of hexanes:ethyl acetate (20:1 to 5:1) to give 3.5 g (63%) of pure 3-dodecyloxy-2-decyloxy-1-propanol.

Workup

  1. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-410a37581043495b8e6864ae44c0e85f
Source dataset
uspto-grants-1998_06
Patent number
US05770584

Reaction notes

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