3,5-Dimethyl-4-hydroxybenzaldehyde → HCID 18533316, compound

HRID 413605Notes

Reaction equation

HRID 413605 reaction equation
CC(C)([O-])C.[K+].[CH:7]([C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([OH:16])=[C:11]([CH3:17])[CH:10]=1)=[O:8].Br[CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>CN(C=O)C>[CH:7]([C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([O:16][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:11]([CH3:17])[CH:10]=1)=[O:8]

Participants

5

Reactant 3

HCID 752223,5-Dimethyl-4-hydroxybenzaldehydeHCID 84580Ethyl 5-bromovalerateHCID 23665647Potassium tert-butoxide

Product 1

HCID 18533316HCID 18533316, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
110 °C

Procedure

Potassium tert-butoxide (2.1 g, mw 112.2, 18 mmol) was added to a solution of 4-formyl-2,6-dimethylphenol (2.5 g, mw 150.2, 17 mmol) in dry DMF (15 mL) and the resultant suspension stirred under N2 at 25° C. for 5 minutes. Ethyl 5-bromovalerate (2.8 mL, mw 209.1, ρ 1.32, 18 mmol) dissolved in dry DMF (15 mL) was added, and the reaction heated at 110° C. for 5 hours, following which DMF was removed at 60° C. and 2 mm Hg. The residue was taken up in ethyl acetate (125 mL), washed with water (25 mL), 1 N aqueous NaOH (25 mL), and brine (75 mL), dried over Na2SO4, filtered, and concentrated to yield 4.47 g (97%) of NMR and TLC (Rf 0.58, CHCl3-methanol, 99:1) pure title product as an amber oil.

Workup

  1. additionwas added
  2. customwas removed at 60° C.
  3. washwashed with water (25 mL), 1 N aqueous NaOH (25 mL), and brine (75 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4bf7d584ba31424c8da9d706c90b0c7e
Source dataset
uspto-grants-2003_05
Patent number
US06566494B1

Reaction notes

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