Hydrochloric Acid → Trans 2-carboethoxy-3-carboxy-1,2,3,4-tetrahydronaphthalene

HRID 901992Notes

Reaction equation

HRID 901992 reaction equation
[C:1]([C@H:6]1[C@H:15]([C:16]([O:18]CC)=[O:17])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)([O:3][CH2:4][CH3:5])=[O:2].[OH-].[Na+].Cl>C(O)C.C(OCC)(=O)C>[C:1]([C@H:6]1[C@H:15]([C:16]([OH:18])=[O:17])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12187587Trans 2,3-dicarboethoxy-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 58646746Trans 2-carboethoxy-3-carboxy-1,2,3,4-tetrahydronaphthaleneYield 73%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of trans 2,3-dicarboethoxy-1,2,3,4-tetrahydronaphthalene (2.1 g, 7.6 mmol) in ethanol (10 mL) at room temperature under nitrogen was added 1.0 M aqueous sodium hydroxide solution (7.6 mL, 7.6 mmol). After 16 h, 1.0 M aqueous hydrochloric acid solution (10 mL) was added to quench the reaction mixture. Upon completion of addition, the reaction mixture was concentrated under vacuum to yield a residue. The residue was diluted with ethyl acetate. The organic layer was washed with 1.0 M aqueous hydrochloric acid solution, saturated aqueous ammonium chloride solution and brine, dried over anhydrous magnesium sulfate, and concentrated under vacuum to yield a residue. The residue was purified by silica gel chromatography (50% ethyl acetate in hexane was used) to yield the title compound (1.37 g, 73%). 13C NMR (400 MHz, (CD3)2CO) δ 175.7, 174.7, 135.0, 134.9, 129.3, 129.2, 127.0, 61.0, 42.8, 42.5, 32.2, 14.4. 1H NMR (400 MHz, (CD3)2CO) δ 7.02 (s, 4H), 4.03 (m, 2H), 2.74-3.09 (m, 6H), 1.13 (t, J=7.0 Hz, 6H). MS [M+Na]+, 271.

Workup

  1. customto quench the reaction mixture
  2. additionUpon completion of addition
  3. concentrationthe reaction mixture was concentrated under vacuum
  4. customto yield a residue
  5. washThe organic layer was washed with 1.0 M aqueous hydrochloric acid solution, saturated aqueous ammonium chloride solution and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under vacuum
  8. customto yield a residue
  9. customThe residue was purified by silica gel chromatography (50% ethyl acetate in hexane was used)

Sources & evidence

ORD record
ord-431d6e57f31f48d3abeeba3c2ac7cd80
Source dataset
uspto-grants-2008_04
Patent number
US07365061B2

Reaction notes

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