Sodium Iodide → Ethyl 5-(2-formyl-3-benzyloxyphenoxy)pentanoate

HRID 485158Notes

Reaction equation

HRID 485158 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]=1[CH:4]=[O:5].Br[CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>O.CN(C)C=O>[CH:4]([C:3]1[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:8]=[CH:9][C:2]=1[O:1][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:5]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 84580Ethyl 5-bromovalerateHCID 141628792-(Benzyloxy)-6-hydroxybenzaldehyde

Product 1

HCID 20271552Ethyl 5-(2-formyl-3-benzyloxyphenoxy)pentanoateYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-hydroxy-6-benzyloxybenzaldehyde (3.0 g, 0.013 M), ethyl 5-bromopentanoate (2.75 g, 0.013 M), anhydrous potassium carbonate (2.16 g, 0.0156 M), sodium iodide (0.195 g) and dry dimethylformamide (15 ml) were stirred at 60°-80° C. for 3 hours and then left to stir at room temperature overnight. The mixture was then poured into water (50 ml) and the product extracted with ether (2×80 ml) and the combined extracts washed with 10% aqueous sodium hydroxide (2×20 ml) and then with water to neutrality, dried, and evaporated to give ethyl 5-(2-formyl-3-benzyloxyphenoxy)pentanoate, (4.0 g, 86%) as a pale yellow oil.

Workup

  1. waitleft
  2. stirringto stir at room temperature overnight
  3. extractionthe product extracted with ether (2×80 ml)
  4. washthe combined extracts washed with 10% aqueous sodium hydroxide (2×20 ml)
  5. dry with materialwith water to neutrality, dried
  6. customevaporated

Sources & evidence

ORD record
ord-921ff042aaed49f8af843f4bdc512b3e
Source dataset
uspto-grants-1985_08
Patent number
US04535183

Reaction notes

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