4-Hydroxybenzaldehyde → 4-(6-Hydroxyhexoxy)benzaldehyde

HRID 1867777Notes

Reaction equation

HRID 1867777 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Cl[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN1C(=O)CCC1.O>[OH:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 748286-Chloro-1-hexanol

Product 1

HCID 150510824-(6-Hydroxyhexoxy)benzaldehydeYield 51.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4-Hydroxybenzaldehyde (15 g, 122 mmol) was dissolved in 150 ml of NMP. 6-Chlorohexanol (20.16 g 146 mmol), anhydrous potassium carbonate (20.36 g, 146 mmol) and a catalytic amount of potassium iodide were added. The batch was stirred at 90 C for 24 hours. Water was added to the cooled solution, which was subsequently extracted with 3×100 mls of ethyl acetate. The combined organics were washed with 5% KOH (2×100 mls), brine solution and then dried over magnesium sulfate. The concentrated product was then recrystallized from a 1:1 mixture of ethyl acetate/hexane to give 14 g of an off-white solid.

Workup

  1. extractionwas subsequently extracted with 3×100 mls of ethyl acetate
  2. washThe combined organics were washed with 5% KOH (2×100 mls), brine solution
  3. dry with materialdried over magnesium sulfate
  4. customThe concentrated product was then recrystallized from a 1:1 mixture of ethyl acetate/hexane

Sources & evidence

ORD record
ord-bbba24f045324a448a762aa6c982a7a1
Source dataset
uspto-grants-2009_12
Patent number
US07632875B2

Reaction notes

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