Hydrochloric Acid → 2-Methoxy-4-(2',2',2'-tris(octadecyloxymethyl)ethoxy)benzaldehyde

HRID 537607Notes

Reaction equation

HRID 537607 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][CH3:11])[CH:3]=1.I[CH2:13][C:14]([CH2:55][O:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH3:74])([CH2:35][O: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])[CH2:15][O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C.C(Cl)(Cl)Cl>[CH3:11][O:10][C:4]1[CH:3]=[C:2]([O:1][CH2:13][C:14]([CH2:15][O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])([CH2:55][O:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH3:74])[CH2:35][O: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:9]=[CH:8][C:5]=1[CH:6]=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 5195414-Hydroxy-2-MethoxybenzaldehydeHCID 594992271-[3-Iodo-2,2-bis(octadecyloxymethyl)propoxy]octadecane

Product 1

HCID 866548902-Methoxy-4-(2',2',2'-tris(octadecyloxymethyl)ethoxy)benzaldehydeYield 96.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

4-Hydroxy-2-methoxybenzaldehyde (136 mg, 894 μmol) was dissolved in DMF (10 ml), 1-[3-iodo-2,2-bis(octadecyloxymethyl)propoxy]octadecane (600 mg, 598 μmol) and potassium carbonate (165 mg, 1.19 mmol) were added, and the mixture was stirred at 130° C. for 3 days. The reaction mixture was cooled to room temperature, 1N hydrochloric acid (10 ml) and chloroform (10 ml) were added, and the mixture was stirred. The aqueous layer was removed, and the organic layer was further washed twice with purified water (10 ml). The organic layer was evaporated under reduced pressure, and the residue was precipitated with methanol to give crude crystals of 2-methoxy-4-[2′,2′,2′-tris(octadecyloxymethyl)ethoxy]benzaldehyde (592 mg, 96%). The obtained crude crystals were purified by silica gel column chromatography (chloroform-hexane=2:1-chloroform→hexane-ethyl acetate=10:1).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringthe mixture was stirred
  3. customThe aqueous layer was removed
  4. washthe organic layer was further washed twice with purified water (10 ml)
  5. customThe organic layer was evaporated under reduced pressure
  6. customthe residue was precipitated with methanol

Sources & evidence

ORD record
ord-40cc96fb81194e5c9045640fa8805e67
Source dataset
uspto-grants-2014_10
Patent number
US08859732B2

Reaction notes

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