3-Hydroxybenzaldehyde → Ethyl 4-(3-formylphenoxy)butanoate

HRID 964874Notes

Reaction equation

HRID 964874 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].Br[CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>>[CH:5]([C:4]1[CH:3]=[C:2]([CH:9]=[CH:8][CH:7]=1)[O:1][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:6]

Participants

5

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 10466631Ethyl 4-(3-formylphenoxy)butanoateYield 92.5%

Procedure

3-Hydroxybenzaldehyde (900 mg, 7.37 mmol) is treated with 2.16 g (11.05 mmol) of ethyl 4-bromobutyrate, 3.06 g (22.11 mmol) of potassium carbonate, and a catalytic amount (110 mg 0.74 mmol) of sodium iodide under the same conditions as in Preparation 3 to give a yellow oil. Purification by flash chromatography using hexane/ethyl acetate (10:1) gives 1.61 g of 4-(3-formylphenoxy)butanoic acid, ethyl ester as a light yellow oil. The 1H NMR (300 MHz, CDCl3) is consistent with the desired product; IR (neat) 1730, 1700, 1600, 1580 cm-1 ; MS (CI low res) m/e 237 (M+H), 191, 115.

Workup

  1. customto give a yellow oil
  2. customPurification by flash chromatography

Sources & evidence

ORD record
ord-c2b7e6c9827c418b9958294563faa103
Source dataset
uspto-grants-1998_06
Patent number
US05773001

Reaction notes

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