4-Hydroxybenzaldehyde → HCID 58284274, compound

HRID 2092229Notes

Reaction equation

HRID 2092229 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-71bfd05ae1b94b49bfb1dc6a32b70dbd
Source dataset
uspto-grants-2013_05
Patent number
US08440700B2

Reaction notes

Loading…