4-Hydroxybenzaldehyde → Ethyl 4-(4-formylphenoxy)butanoate

HRID 986558Notes

Reaction equation

HRID 986558 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+].Br[CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CC(=O)CC>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:3][CH:4]=1)=[O:7]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 15517709Ethyl 4-(4-formylphenoxy)butanoateYield 67%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

A solution of 4-hydroxybenzaldehyde (15.0 g, 0.122 mole) in butanone (200 ml) was treated with anhydrous potassium carbonate (18.55 g, 0.134 mole), and the mixture stirred at room temperature for 20 mins. Ethyl 4-bromobutanoate, (24.0 g, 0.122 mole), dissolved in butanone (10 ml), was added dropwise to the stirred mixture over a period of 1 h. The reaction was stirred and refluxed for 6 h, then cooled and partitioned between water and butanone. The organic phase was separated, washed with dilute sodium hydroxide, water, brine and dried, (MgSO4). Evaporation of the solvent in vacuo gave a red oil, which was distilled at 0.05 mm/Hg to yield 19.31 g (67%) of a colourless oil, bp 152°-6° C. υmax (film) 1730, 1685, 1600, 1580, 1508 cm-1 δ (CDCl3) 1.25 (3H, t, J 7 Hz, ester CH3) 2.18 (2H, bt, J6 Hz, OCH2CH2), 2.49 (2H, bt, J6 Hz, CH2CO2), 4.09 (2H, t, J6 Hz, OCH2), 4.11 (2H, q, J7 Hz, ester CH2), 7.38 (4H, ABq, Δυ75 Hz, J9 Hz, C6H4), 9.90 (1H, s, CHO)

Workup

  1. additionwas added dropwise to the stirred mixture over a period of 1 h
  2. stirringThe reaction was stirred
  3. temperaturerefluxed for 6 h
  4. temperaturecooled
  5. custompartitioned between water and butanone
  6. customThe organic phase was separated
  7. washwashed with dilute sodium hydroxide, water, brine
  8. customdried
  9. customEvaporation of the solvent in vacuo
  10. customgave a red oil, which
  11. distillationwas distilled at 0.05 mm/Hg

Sources & evidence

ORD record
ord-771f1db8dcfe4488a174e04e2d522dc3
Source dataset
uspto-grants-1987_12
Patent number
US04713486

Reaction notes

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