Cetyl Alcohol → HCID 117676213, compound

HRID 1501284Notes

Reaction equation

HRID 1501284 reaction equation
[CH2:1]([OH:17])[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].[I-].ClC1C=CC=C[N+]=1C.[OH:27][C:28]1[C:29]([CH3:44])=[C:30]2[C:35](=[C:36]([CH3:39])[C:37]=1[CH3:38])[O:34][C:33]([CH3:43])([C:40](O)=[O:41])[CH2:32][CH2:31]2.CCCCCC>CN(C)C1C=CN=CC=1.O1CCOCC1.C(OCC)(=O)C>[CH2:1]([O:17][C:40]([C:33]1([CH3:43])[CH2:32][CH2:31][C:30]2[C:35](=[C:36]([CH3:39])[C:37]([CH3:38])=[C:28]([OH:27])[C:29]=2[CH3:44])[O:34]1)=[O:41])[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

8

Reactant 4

HCID 2682Cetyl AlcoholHCID 8058HexaneHCID 40634TroloxHCID 1670692-Chloro-1-methylpyridinium iodide

Product 1

HCID 117676213HCID 117676213, compoundYield 65.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

Under electromagnetic stirring, to a 100 mL reaction flask hexadecanol (970 mg, 4 mmol), 4-dimethylaminopyridine (1466 mg, 12 mmo), 2-chloro-1-methylpyridinium iodide (1533 mg, 6 mmol) and dioxane (20 mL) were added, and then to the reaction solution a solution of (±)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (1001 mg, 4 mmol) in dioxane (20 mL) was slowly dropwise added. The reaction mixture was reacted for 12 h at room temperature under the protection of nitrogen gas and electromagnetic stirring. The solvent (dioxane) was removed by a rotary evaporator, and thereto diethyl ether (50 mL) was added. The resulting mixture was stirred for 2 h, and the precipitate was removed by filtration. The filtrate was concentrated to 10 mL, and isolated by column chromatography (the stationary phase was 230-400 mesh silica gel, the eluent was hexane:ethyl acetate=10:1), to obtain (±)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid hexadecyl ester (1242 mg, yield 65.4%).

Workup

  1. additionwere added
  2. customThe reaction mixture was reacted for 12 h at room temperature under the protection of nitrogen gas and electromagnetic stirring
  3. customThe solvent (dioxane) was removed by a rotary evaporator
  4. additiondiethyl ether (50 mL) was added
  5. customthe precipitate was removed by filtration
  6. concentrationThe filtrate was concentrated to 10 mL
  7. customisolated by column chromatography (the stationary phase

Sources & evidence

ORD record
ord-6be803af474a4fc38cc030b8afc81754
Source dataset
uspto-grants-2015_12
Patent number
US09206192B2

Reaction notes

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