4-Hydroxybenzaldehyde → 4-(2-Hydroxypropoxy)benzaldehyde

HRID 2362821Notes

Reaction equation

HRID 2362821 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[OH:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1.Cl[CH2:17][CH:18]([OH:20])[CH3:19].C(=O)(O)[O-].[Na+]>CN(C=O)C>[OH:20][CH:18]([CH3:19])[CH2:17][O:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 10340Sodium CarbonateHCID 313701-Chloro-2-propanolHCID 516892Sodium Bicarbonate

Product 1

HCID 574320794-(2-Hydroxypropoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

18.30 g (172.6 mmol) of sodium carbonate are added to a solution of 7.03 g (57.5 mmol) of p-hydroxybenzaldehyde and 6.80 g (71.9 mmol) of 1-chloro-2-propanol (technical grade, about 70% pure, isomer mixture with 2-chloro-1-propanol) in 125 ml of dry DMF, and the mixture is stirred at +130° C. for 20 h. After cooling to RT, 100 ml of saturated sodium bicarbonate solution are added and the mixture is extracted with ethyl acetate (three times, 100 ml each). The combined organic phases are dried over magnesium sulphate. After removal of the solvent on a rotary evaporator, the crude product is purified chromatographically on silica gel 60 (mobile phase gradient cyclohexane/ethyl acetate 5:1→2:1).

Workup

  1. extractionthe mixture is extracted with ethyl acetate (three times, 100 ml each)
  2. dry with materialThe combined organic phases are dried over magnesium sulphate
  3. customAfter removal of the solvent
  4. customon a rotary evaporator
  5. customthe crude product is purified chromatographically on silica gel 60 (mobile phase gradient cyclohexane/ethyl acetate 5:1→2:1)

Sources & evidence

ORD record
ord-4332f7271d5a40218e0e462a3f80a578
Source dataset
uspto-grants-2014_04
Patent number
US08691850B2

Reaction notes

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