Water → HCID 59539818, compound

HRID 2204925Notes

Reaction equation

HRID 2204925 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.[I-].[K+]>[OH:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11]

Participants

7

Reactant 4

HCID 962WaterHCID 1183VanillinHCID 11430Potassium CarbonateHCID 7416311-Bromo-1-undecanol

Product 1

HCID 59539818HCID 59539818, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

25.9 g (170 mmol) of 4-hydroxy-3-methoxybenzaldehyde and 38.9 g (155 mmol) of 11-bromoundecan-1-ol are dissolved in 200 mL of N,N-dimethylformamide. 23.57 g (170 mmol) of potassium carbonate and 2.47 g (15 mmol) of potassium iodide are added and the suspension is heated to 80° C. After 12 h, the reaction mixture is cooled to room temperature and poured to icy water. The precipitate is filtered off, digested in 500 mL of water and the mixture was neutralized with hydrochloric acid 37%. The precipitate is filtered off, washed with water and dried overnight at 40° C. 48.5 g of 4-[(11-hydroxyundecyl)oxy]-3-methoxybenzaldehyde are obtained as a slightly pink solid (97% yield). This material proves chromatographically homogenous and displays spectral characteristics consistent with its assigned structure.

Workup

  1. temperaturethe reaction mixture is cooled to room temperature
  2. filtrationThe precipitate is filtered off
  3. filtrationThe precipitate is filtered off
  4. washwashed with water
  5. customdried overnight at 40° C

Sources & evidence

ORD record
ord-e59a864795e24433ae504a8bff41f4b4
Source dataset
uspto-grants-2016_06
Patent number
US09366906B2

Reaction notes

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