Methanol → HCID 18914709, compound

HRID 978767Notes

Reaction equation

HRID 978767 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][CH:7]1[CH2:16][CH2:15][C:14]2[CH:13]=[C:12]([C:17]([O:19]CC)=[O:18])[CH:11]=[CH:10][C:9]=2[CH2:8]1.[OH-].[Na+].CO>O>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][CH:7]1[CH2:16][CH2:15][C:14]2[CH:13]=[C:12]([C:17]([OH:19])=[O:18])[CH:11]=[CH:10][C:9]=2[CH2:8]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 70388212HCID 70388212, compound

Product 1

HCID 18914709HCID 18914709, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.31 g of ethyl 6-(1-imidazolylmethyl)-5,6,7,8-tetrahydro-2-naphthalenecarboxylate, 0.49 g of sodium hydroxide, 60 ml of methanol and 20 ml of water was heated under reflux for 4 hours. Methanol was distilled off in vacuo and 50 ml of water was added to the residue. Chloroform was added to the mixture and the aqueous layer was separated. The aqueous solution was adjusted to pH 6 with 2 normal hydrochloric acid. The precipitate formed was collected by filtration and washed with water to give 1.14 g of 6-(1-imidazolylmethyl)-5,6,7,8-tetrahydro-2-naphthalenecarboxylic acid as a colorless powder with m.p. 224°-226° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. distillationMethanol was distilled off in vacuo and 50 ml of water
  4. additionwas added to the residue
  5. additionChloroform was added to the mixture
  6. customthe aqueous layer was separated
  7. customThe precipitate formed
  8. filtrationwas collected by filtration
  9. washwashed with water

Sources & evidence

ORD record
ord-14292e1f2e244b34a7692e412ff8d6aa
Source dataset
uspto-grants-1987_05
Patent number
US04665188

Reaction notes

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