4-Hydroxybenzaldehyde → HCID 58284274, compound

HRID 508149Notes

Reaction equation

HRID 508149 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][C:12]([CH3:15])([OH:14])[CH3:13].C(=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[OH:14][C:12]([CH3:15])([CH3:13])[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 10340Sodium CarbonateHCID 684091-Chloro-2-methylpropan-2-olHCID 516892Sodium Bicarbonate

Product 1

HCID 58284274HCID 58284274, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5.00 g (40.94 mmol) of 4-hydroxybenzaldehyde, 4.44 g (40.94 mmol) of 1-chloro-2-methyl-2-propanol and 6.08 g (57.32 mmol) of sodium carbonate are initially charged in 50 ml of dry DMF and stirred under reflux for 24 h. After cooling to RT, 20 ml of ethyl acetate and 20 ml of sat. aqueous sodium bicarbonate solution are added. The phases are separated, and the organic phase is dried over magnesium sulfate. After removal of the solvent, the residue is purified by column chromatography on silica gel 60 (mobile phase gradient: cyclohexane/ethyl acetate 5:1→1:1). This gives a reddish solid which is used without further purification for the subsequent step.

Workup

  1. temperatureunder reflux for 24 h
  2. customThe phases are separated
  3. dry with materialthe organic phase is dried over magnesium sulfate
  4. customAfter removal of the solvent
  5. customthe residue is purified by column chromatography on silica gel 60 (mobile phase gradient: cyclohexane/ethyl acetate 5:1→1:1)
  6. customThis gives a reddish solid which
  7. customis used without further purification for the subsequent step

Sources & evidence

ORD record
ord-5b55655856154b78a9f3cbfd51962cfd
Source dataset
uspto-grants-2015_08
Patent number
US09095582B2

Reaction notes

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