Dimethylformamide → 3,5-Di(docosyloxy)benzylchloride

HRID 537602Notes

Reaction equation

HRID 537602 reaction equation
[CH2:1]([O:23][C:24]1[CH:25]=[C:26]([CH:29]=[C:30]([O: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][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH:31]=1)[CH2:27]O)[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][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].S(Cl)([Cl:57])=O.CN(C=O)C>C(Cl)(Cl)Cl>[CH2:1]([O:23][C:24]1[CH:25]=[C:26]([CH:29]=[C:30]([O: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][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH:31]=1)[CH2:27][Cl:57])[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][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 49844210(3,5-Bis(docosyloxy)phenyl)methanol

Product 1

HCID 672488813,5-Di(docosyloxy)benzylchlorideYield 99%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3,5-Di(docosyloxy)benzyl alcohol (500 mg, 0.66 mmol) was dissolved in chloroform (5 ml), thionyl chloride (71 μl, 0.99 mmol) and DMF (10 μl, 0.13 mmol) were added dropwise, and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated, and the residue was precipitated with acetonitrile to give 3,5-di(docosyloxy)benzylchloride (505 mg, 0.65 mmol, 99%).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was precipitated with acetonitrile

Sources & evidence

ORD record
ord-a55ffefb20634d1eaf92056681814744
Source dataset
uspto-grants-2014_10
Patent number
US08859732B2

Reaction notes

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