Hydrochloric Acid → [5-(carboxymethoxy)-1,2,3,4-tetrahydro-2-naphthyl]methyl N,N-diphenylcarbamate

HRID 963696Notes

Reaction equation

HRID 963696 reaction equation
[C:1]1([N:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:8](=[O:28])[O:9][CH2:10][CH:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[O:21][CH2:22][C:23]([O:25]CC)=[O:24])[CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>C(O)C>[C:29]1([N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8](=[O:28])[O:9][CH2:10][CH:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[O:21][CH2:22][C:23]([OH:25])=[O:24])[CH2:12]2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70187804[5-(ethoxycarbonylmethoxy)-1,2,3,4-tetrahydro-2-naphthyl]methyl N,N-diphenylcarbamate

Product 1

HCID 44402710[5-(carboxymethoxy)-1,2,3,4-tetrahydro-2-naphthyl]methyl N,N-diphenylcarbamateYield 84.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of [5-(ethoxycarbonylmethoxy)-1,2,3,4-tetrahydro-2-naphthyl]methyl N,N-diphenylcarbamate (59 mg) and 1N sodium hydroxide solution (0.15 ml) in ethanol (1.5 ml) was stirred at room temperature for 1 hour and neutralized with 1N hydrochloric acid (0.15 ml), then extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was powdered from n-hexane to afford [5-(carboxymethoxy)-1,2,3,4-tetrahydro-2-naphthyl]methyl N,N-diphenylcarbamate (47 mg) as a colorless powder. mp: 137°-141.5° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-a81b8623739b4051a5ad24536308374b
Source dataset
uspto-grants-1998_06
Patent number
US05763489

Reaction notes

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