Sodium Hydroxide → 3,4-Dihydro-6-(phenylmethoxy)-2-naphthalenecarboxylic acid

HRID 1638789Notes

Reaction equation

HRID 1638789 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15](O)[CH:14]([C:20]([OH:22])=[O:21])[CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16]([CH:15]=[C:14]([C:20]([OH:22])=[O:21])[CH2:13][CH2:12]2)=[CH:17][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19841196HCID 19841196, compound

Product 1

HCID 146761973,4-Dihydro-6-(phenylmethoxy)-2-naphthalenecarboxylic acidYield 79.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl ester of 6-benzyloxy-1-hydroxy-1,2,3,4-tetrahydro-2-naphthoic acid (0.6 g) is dissolved in methanol (50 ml). To the solution is added an aqueous solution (10 ml) of sodium hydroxide (2 g), and the mixture is left standing for 30 minutes at room temperature. The resultant is concentrated under reduced pressure. The concentrate is diluted with water (50 ml). The precipitating crystals are collected by filtration. This product is dissolved in a mixture of dioxane (50 ml) and concentrated hydrochloric acid (2 ml). The mixture is left standing for 5 minutes at 80° C. and then for 30 minutes at room temperature. The resultant is concentrated under reduced pressure. Water (50 ml) is added to the concentrate. The precipitating crystals are collected by filtration to give 7-benzyloxy-1,2-dihydro-3-naphthoic acid (0.45 g) as colorless crystals, followed by recrystallization from a mixture of methanol and acetone to afford colorless needles, m.p. 202°-205° C.

Workup

  1. waitthe mixture is left
  2. concentrationThe resultant is concentrated under reduced pressure
  3. additionThe concentrate is diluted with water (50 ml)
  4. filtrationThe precipitating crystals are collected by filtration
  5. dissolutionThis product is dissolved in a mixture of dioxane (50 ml) and concentrated hydrochloric acid (2 ml)
  6. waitThe mixture is left
  7. waitstanding for 5 minutes at 80° C.
  8. waitfor 30 minutes at room temperature
  9. concentrationThe resultant is concentrated under reduced pressure
  10. additionWater (50 ml) is added to the concentrate
  11. filtrationThe precipitating crystals are collected by filtration

Sources & evidence

ORD record
ord-c2d425b448184586907ebbbe175e633e
Source dataset
uspto-grants-1989_11
Patent number
US04880809

Reaction notes

Loading…