4-Hydroxybenzaldehyde → 4-TETRADECYLOXYBENZALDEHYDE

HRID 1833708Notes

Reaction equation

HRID 1833708 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C[O-].[Na+].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>CN(C)C=O>[CH2:27]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 8208Myristyl bromideHCID 10942334Sodium Methoxide

Product 1

HCID 110453834-TETRADECYLOXYBENZALDEHYDE

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 50 g (0.41 mole) of p-hydroxybenzaldehyde, 22.2 g (0.41 mole) of sodium methoxide and 500 ml of dried dimethylformamide was added 114 g (0.41 mole) of 1-bromotetradecane. The mixture was refluxed for 3 hours, then allowed to stand at room temperature overnight after which it was poured into ice-water and extracted with diethyl ether. The ether layer was washed with water, 5% potassium hydroxide, and saline, and dried over sodium sulfate, filtered and evaporated. The residue is recrystallized from hexane to give 4-tetradecyloxybenzaldehyde.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. extractionextracted with diethyl ether
  3. washThe ether layer was washed with water, 5% potassium hydroxide, and saline
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is recrystallized from hexane

Sources & evidence

ORD record
ord-9fc7382099a34bbd934f448ffdc99c61
Source dataset
uspto-grants-1978_01
Patent number
US04066788

Reaction notes

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