Ethyl 4-hydroxyphenylacetate → Ethyl 4-(3,4-methylenedioxybenzyloxy)-phenylacetate

HRID 2412545Notes

Reaction equation

HRID 2412545 reaction equation
[Na].[OH: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.[CH2:15]1[O:25][C:24]2[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][C:17]=2[O:16]1>C(O)C>[CH2:15]1[O:25][C:24]2[CH:23]=[CH:22][C:19]([CH2:20][O:2][C:3]3[CH:4]=[CH:5][C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:7][CH:8]=3)=[CH:18][C:17]=2[O:16]1

Participants

5

Reactant 3

HCID 28310Ethyl 4-hydroxyphenylacetateHCID 887131,3-Benzodioxole, 5-(chloromethyl)-HCID 5360545Sodium

Product 1

HCID 20431667Ethyl 4-(3,4-methylenedioxybenzyloxy)-phenylacetateYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a sodium alcoholate solution of 2.16 gm (94 mmol) of sodium in 100 ml ethanol were added 16.9 gm (94 mmol) of ethyl 4-hydroxyphenylacetate with agitation. Then, 16.0 gm (94 mmol) of 3,4-methylenedioxybenzyl chloride were added dropwise, and the mixture was maintained at the boiling temperature for eight hours. After evaporation, taking up of the residue in ether, washing with Na2CO3 solution and water, treating of the ether solution with activated charcoal, and evaporation, the residue was distilled at 0.13 mbar. The volatile material that was removed by distillation until a pot temperature of 240° C. was reached, amounted to 5.9 grams. The residue of 21 gm was chromatographed in a column of silica gel (granule size 0.063 to 0.200 mm, available from Merck & Co.), with methylene chloride as solvent. An amount of 16.7 gm of ethyl 4-(3,4-methylenedioxybenzyloxy)-phenylacetate (57% of theory), with a melting point of 49° to 52° C. and refractive index nD20 =1.5643, was obtained.

Workup

  1. temperaturethe mixture was maintained at the boiling temperature for eight hours
  2. customAfter evaporation
  3. washwashing with Na2CO3 solution and water
  4. additiontreating of the ether solution with activated charcoal, and evaporation
  5. distillationthe residue was distilled at 0.13 mbar
  6. customThe volatile material that was removed by distillation until a pot temperature of 240° C.
  7. customThe residue of 21 gm was chromatographed in a column of silica gel (granule size 0.063 to 0.200 mm, available from Merck & Co.), with methylene chloride as solvent

Sources & evidence

ORD record
ord-ac812efd87fa40fbbfd0213af4556bab
Source dataset
uspto-grants-1985_01
Patent number
US04493823

Reaction notes

Loading…