3-Hydroxybenzaldehyde → 3-butoxybenzaldehyde

HRID 1073236Notes

Reaction equation

HRID 1073236 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[H-].[Na+].Br[CH2:13][CH2:14][CH2:15][CH3:16]>CN(C)C=O>[CH2:13]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])[CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 8002Butyl bromideHCID 24758Sodium hydride

Product 1

HCID 27572023-butoxybenzaldehydeYield 89.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

3-Hydroxybenzaldehyde (61 g) was added over 40 minutes to a suspension of sodium hydride (13.0 g) in dimethylformamide (700 cm3), the temperature of the reaction mixture being kept below 10° C. by means of a CO2 /oxitol bath. After stirring for 35 minutes, 1-bromobutane (73 g) was added dropwise over one hour and the mixture was then stirred at room temperature for 2.5 hours followed by heating at 85° C. for a further 2.5 hours. The resulting mixture was poured into ice water (1000 cm3) and was allowed to stand overnight before extracting with 40°-60° petrol/ether (3:1) (5×200 cm3). The combined organic layers were washed with 1M sodium hydroxide solution containing sodium chloride, dried over sodium sulphate, treated with activated charcoal, filtered and then evaporated down to give a golden brown mobile oil (79.7 g).

Workup

  1. customthe temperature of the reaction mixture being kept below 10° C. by means of a CO2 /oxitol bath
  2. stirringthe mixture was then stirred at room temperature for 2.5 hours
  3. waitto stand overnight
  4. extractionbefore extracting with 40°-60° petrol/ether (3:1) (5×200 cm3)
  5. washThe combined organic layers were washed with 1M sodium hydroxide solution
  6. additioncontaining sodium chloride
  7. dry with materialdried over sodium sulphate
  8. additiontreated with activated charcoal
  9. filtrationfiltered
  10. customevaporated down

Sources & evidence

ORD record
ord-9dccdd55dff14f70b95d47d2a639a3ed
Source dataset
uspto-grants-1990_11
Patent number
US04968698

Reaction notes

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