3-Hydroxybenzaldehyde → 3-Propoxybenzaldehyde

HRID 1666872Notes

Reaction equation

HRID 1666872 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C([O-])([O-])=O.[K+].[K+].CN(C=O)C.I[CH2:22][CH2:23][CH3:24]>C1(C)C=CC=CC=1.O>[CH2:22]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])[CH2:23][CH3:24]

Participants

7

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 336431-Iodopropane

Product 1

HCID 27604693-Propoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

Combine 3-hydroxybenzaldehyde (790 g), K2CO3, (1627 g) and DMF (8 L). Add 1-iodopropane (1000 g) and heat to 105° C. and stir for 4 h. Cool to about 50° C. and add water (15 L), continue cooling to about room temperature and add toluene (10 L). Separate the organic layer and extract the aqueous phase with toluene (2×10 L), combine organic phases and wash with NaOH 1N (2×5.8 L), concentrate the combined organic layers in vacuo to afford the title compound.

Workup

  1. temperaturecontinue cooling to about room temperature
  2. customSeparate the organic layer
  3. extractionextract the aqueous phase with toluene (2×10 L)
  4. washwash with NaOH 1N (2×5.8 L)
  5. concentrationconcentrate the combined organic layers in vacuo

Sources & evidence

ORD record
ord-2d24e54df193457bb3feb4908fa8a161
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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