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

HRID 1810714Notes

Reaction equation

HRID 1810714 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+].O>CN1C(=O)CCC1>[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

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 748286-Chloro-1-hexanol

Product 1

HCID 150510824-(6-Hydroxyhexoxy)benzaldehydeYield 51.6%

Reagents, catalysts & solvents 1

HCID 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 K2CO3 (20.36 g, 146 mmol) and a catalytic amount of KI were added. The batch was stirred at 90 C for 24 hours. Water was added to the cooled solution, which was subsequently extracted with EtOAc (3×100 mL). The combined extracts were washed with 5% KOH (2×100 mL), brine solution and then dried over MgSO4. The concentrated product was then recrystallized from a 1:1 mixture of EtOAc/hexane to give 14 g of an off-white solid.

Workup

  1. extractionwas subsequently extracted with EtOAc (3×100 mL)
  2. washThe combined extracts were washed with 5% KOH (2×100 mL), brine solution
  3. dry with materialdried over MgSO4
  4. customThe concentrated product was then recrystallized from a 1:1 mixture of EtOAc/hexane

Sources & evidence

ORD record
ord-a718f0ff25434af59cb606b0ad09fd73
Source dataset
uspto-grants-2013_01
Patent number
US08362151B2

Reaction notes

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