Hexamethylenetetramine → Ethyl 2-(4-formylphenyl)acetate

HRID 377608Notes

Reaction equation

HRID 377608 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1.C1N2CN3CN(C2)CN1C3.C(=O)([O-])[O-:26].[Na+].[Na+]>C(O)(=O)C>[CH:2]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1)=[O:26]

Participants

5

Reactant 3

HCID 4101HexamethylenetetramineHCID 10340Sodium CarbonateHCID 15712209Ethyl 2-(4-(bromomethyl)phenyl)acetate

Product 1

HCID 11310039Ethyl 2-(4-formylphenyl)acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

25.7 g of ethyl 4-bromomethylphenylacetate and 28 g of hexamethylenetetramine are dissolved in 200 ml of 20% acetic acid, heated to 100° C. with stirring and stirred for four hours. The reaction solution is allowed to cool and sufficient sodium carbonate is added until a saturated solution is obtained. This solution is extracted with ether, dried and the ether is then removed. The residue is purified by chromatography (silica gel/methyl t-butyl ether/ether 1:1).

Workup

  1. stirringstirred for four hours
  2. temperatureto cool
  3. customis obtained
  4. extractionThis solution is extracted with ether
  5. customdried
  6. customthe ether is then removed
  7. customThe residue is purified by chromatography (silica gel/methyl t-butyl ether/ether 1:1)

Sources & evidence

ORD record
ord-f366f9710245485a8febd1a7159c7a7d
Source dataset
uspto-grants-2000_02
Patent number
US06028080

Reaction notes

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