4-Hydroxybenzaldehyde → Methyl 2-(4-formylphenoxy)acetate

HRID 992721Notes

Reaction equation

HRID 992721 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC(S(O)(=O)=O)=CC=1.II.[CH3:29][O:30][C:31](=[O:34])[CH2:32]Br>O.C1(C)C=CC=CC=1>[C:31]([CH2:32][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)([O:30][CH3:29])=[O:34]

Participants

8

Reactant 5

HCID 1264-HydroxybenzaldehydeHCID 807IodineHCID 6101p-Toluenesulfonic acidHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Product 1

HCID 758214Methyl 2-(4-formylphenoxy)acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

4-Hydroxybenzaldehyde (250 g, 2.05 M), potassium carbonate (565 g, 4.09 M), toluene (2.5 L), p-toluenesulfonic acid (39 g, 0.21 M) and iodine (2 g, catalytic) were taken in a 5 L 4-neck round bottom flask with mechanical stirrer and a Dean-Stark condenser. Methylbromoacetate (314 g, 2.05 M) was added and the reaction was refluxed for 6-8 hours, under azeotropic removal of water, while monitoring the reaction on TLC. After the completion of the reaction, water was added and the organic layer separated while the aq. layer was extracted with toluene (2×500 ml). The combined organic layers were washed with brine and concentrated under vacuum to yield 4-((carbomethoxy)methoxy)benzaldehyde as an oily material (385 g, Y=97%, P=99%).

Workup

  1. customthe reaction on TLC
  2. additionwas added
  3. customthe organic layer separated while the aq. layer
  4. extractionwas extracted with toluene (2×500 ml)
  5. washThe combined organic layers were washed with brine
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-338d21bea2d64dcdbef54e29d533f676
Source dataset
uspto-grants-2002_10
Patent number
US06469167B1

Reaction notes

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