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Chemistry
Organic Building Blocks
Aryls
Ethyl 4-(benzyloxy)-3-methoxybenzoate
Chemistry
Organic Building Blocks
Aryls
Esters Ethers Benzene Compounds

[ CAS No. 185033-64-1 ] {[proInfo.proName]}

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Chemical Structure| 185033-64-1
Chemical Structure| 185033-64-1
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Product Details of [ 185033-64-1 ]

CAS No. :185033-64-1 MDL No. :MFCD06204301
Formula : C17H18O4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 286.32 Pubchem ID :-
Synonyms :

Safety of [ 185033-64-1 ]

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Application In Synthesis of [ 185033-64-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 185033-64-1 ]

[ 185033-64-1 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 617-05-0 ]
  • [ 100-44-7 ]
  • [ 185033-64-1 ]
Reference： [1]Molecular Crystals and Liquid Crystals (1969-1991),1982,vol. 99,p. 279 - 284
  • 2
  • [ 617-05-0 ]
  • [ 185033-64-1 ]
YieldReaction ConditionsOperation in experiment
B. Benzylation of <strong>[617-05-0]ethyl-3-methoxy-4-hydroxybenzoate</strong> to Yield ethyl-3-methoxy-4-benzyloxybenzoate.
(ii) Benzylation of <strong>[617-05-0]ethyl-3-methoxy-4-hydroxybenzoate</strong> to Yield ethyl-3-methoxy-4-benzyloxybenzoate.
(ii) Benzylation of <strong>[617-05-0]ethyl-3-methoxy-4-hydroxybenzoate</strong> to yield ethyl-3-methoxy-4-benzyloxybenzoate.
B. Benzylation of <strong>[617-05-0]ethyl-3-methoxy-4-hydroxybenzoate</strong> to yield ethyl-3-methoxy-4-benzyloxybenzoate.
B. Benzylation of <strong>[617-05-0]ethyl-3-methoxy-4-hydroxybenzoate</strong> to Yield Ethyl-3-methoxy-4-benzyloxybenzoate.
B. Benzylation of Ethyl-3-methoxy-4-hydroxybenzoate to Yield Ethyl-3-methoxy-4-benzyloxybenzoate.
B. Benzylation of <strong>[617-05-0]ethyl-3-methoxy-4-hydroxybenzoate</strong> to yield ethyl-3-methoxy-4-benzyloxybenzoate.

Reference： [1]Patent: US2004/106601,2004,A1
[2]Patent: US2004/224943,2004,A1
[3]Patent: US2004/229866,2004,A1
[4]Patent: US2004/254173,2004,A1
[5]Patent: US2004/138210,2004,A1
[6]Patent: US2004/138209,2004,A1
[7]Patent: US6638928,2003,B1
  • 3
  • [ 617-05-0 ]
  • [ 100-39-0 ]
  • [ 43039-98-1 ]
  • [ 185033-64-1 ]
YieldReaction ConditionsOperation in experiment
The product so obtained was reacted with ethyl 2-thiazolyl ketone using the procedure described in Example 4 except that the lithiation step and addition of the above mentioned ketone were conducted at -110 C. The mixture was stirred at -110 C. for 30 minutes and then allowed to warm to -20 C. The mixture was poured into a saturated aqueous ammonium chloride solution. The remaining procedure was as described in Example 4. There was thus obtained the required starting material as an oil in 42% yield. jj. The product gave the following NMR data: (CDCl3 delta values) 0.8 (t, 3H), 2.4 (m, 1H), 2.7 (m, 1H), 3.2 (s, 3H), 3.85 (s, 3H), 5.1 (s, 2H), 6.8 (d, 1H), 6.9 (d, 1H), 7.0 (d, 1H), 7.25 (d, 1H), 7.3-7.45 (m, 5H). 7.7 (d, 1H). The 2-[1-(4-benzyloxy-3-methoxyphenyl)-1-hydroxypropyl]thiazole used as a starting material was obtained as follows: Benzyl bromide was reacted with <strong>[617-05-0]ethyl vanillate</strong> using the conditions described in Example 1 to give ethyl 4-benzyloxy-3-methoxybenzoate in 97% yield m.p. 72-74 C. Following the procedures described in the portion of Example 6 which is concerned with the preparation of starting materials the product so obtained was reacted with thiazol-2-yl-lithium and the resultant product was reacted with ethylmagnesium iodide to give the required starting material as an oil in 20% yield.
Reference： [1]Patent: US5089513,1992,A
  • 4
  • [ 617-05-0 ]
  • [ 100-39-0 ]
  • [ 185033-64-1 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In acetone; B. Benzylation of <strong>[617-05-0]ethyl-3-methoxy-4-hydroxybenzoate</strong> to yield ethyl-3-methoxy-4-benzyloxybenzoate A solution of 118 g of <strong>[617-05-0]ethyl-3-methoxy-4-hydroxybenzoate</strong> and 86 mL of benzyl bromide in 600 mL of acetone containing a suspension of 124 g of potassium carbonate was heated at reflux overnight. The mixture was filtered, the filtrate concentrated and the residue recrystallized from acetone.
Reference： [1]Patent: US2004/106602,2004,A1
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 4080 - 4083

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Technical Information

• Acyl Group Substitution • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • Friedel-Crafts Reaction • Hydrogenolysis of Benzyl Ether • Nomenclature of Ethers • Preparation of Alkylbenzene • Preparation of Ethers • Reactions of Benzene and Substituted Benzenes • Reactions of Ethers • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Vilsmeier-Haack Reaction
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