4-Hydroxybenzaldehyde → p-(Hexyloxy)benzaldehyde

HRID 2092955Notes

Reaction equation

HRID 2092955 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)=[O:2].I[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C([O-])([O-])=O.[K+].[K+].O>C(#N)C>[CH2:11]([O:9][C:6]1[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 125271-Iodohexane

Product 1

HCID 79816p-(Hexyloxy)benzaldehydeYield 98.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-formyl-phenol (5 g, 41 mmol), iodohexane (10.5 g, 49 mmol) and K2CO3 (8.5 g, 61 mmol) in acetonitrile (150 ml) were refluxed overnight under N2. After being cooled to room temperature, water (10 ml) was added and acetonitrile was evaporated. Water (150 ml) and Et2O (150 ml) were then added. The ethereal layer was extracted and washed with water (2×100 ml), brine (100 ml), dried over MgSO4, filtered and evaporated to dryness to afford 8.3 g (98%) of compound 1 as a slightly yellow oil after drying at 80° C. under vacuum.

Workup

  1. customacetonitrile was evaporated
  2. additionWater (150 ml) and Et2O (150 ml) were then added
  3. extractionThe ethereal layer was extracted
  4. washwashed with water (2×100 ml), brine (100 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-3a267a34a0e2465c8278b4180211cbcc
Source dataset
uspto-grants-2013_05
Patent number
US08440843B2

Reaction notes

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