Sodium Hydroxide → 6-Hydroxy-3,4-dihydronaphthalene-2-carboxylic acid

HRID 1638788Notes

Reaction equation

HRID 1638788 reaction equation
[OH-].[Na+].C([O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17](O)[CH:16]([C:22]([OH:24])=[O:23])[CH2:15][CH2:14]2)C1C=CC=CC=1>CO>[OH:10][C:11]1[CH:12]=[C:13]2[C:18]([CH:17]=[C:16]([C:22]([OH:24])=[O:23])[CH2:15][CH2:14]2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19841196HCID 19841196, compound

Product 1

HCID 198411996-Hydroxy-3,4-dihydronaphthalene-2-carboxylic acidYield 62.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An aqueous solution (10 ml) of sodium hydroxide (3 g) is added to a solution of methyl ester of 6-benzyloxy-1-hydroxy-1,2,3,4-tetrahydro-2-naphthoic acid (1 g) dissolved in methanol (80 ml) and the mixture is left standing. After 30 minutes, the mixture is concentrated under reduced pressure. Water (50 ml) is added to the mixture, and then precipitating crystals are collected by filtration. The crystals are washed with water and acetone. The crystals (0.9 g) is added to a mixture of methanol (75 ml), water (25 ml) and 10% palladium carbon (50% water-content) (1 g). The mixture is catalytically hydrogenated at room temperature under atomospheric pressure of hydrogen gas. After hydrogen absorption has ceased, the catalyst is filtered off, and the filtrate is concentrated under reduced pressure. To the residue are added dioxane (30 ml), concentrated hydrochloric acid (2 ml) and water (10 ml), and the mixture is left standing at room temperature for one hour. The resultant is concentrated under reduced pressure. The precipitating crystals are treated with water (10 ml) and collected by filtration to give 7-hydroxy-1,2-dihydro-3-naphthoic acid (0.4 g) as colorless prisms, m.p. 195°-197° C.

Workup

  1. waitthe mixture is left
  2. concentrationthe mixture is concentrated under reduced pressure
  3. additionWater (50 ml) is added to the mixture
  4. customprecipitating crystals
  5. filtrationare collected by filtration
  6. washThe crystals are washed with water and acetone
  7. additionThe crystals (0.9 g) is added to a mixture of methanol (75 ml), water (25 ml) and 10% palladium carbon (50% water-content) (1 g)
  8. customis catalytically hydrogenated at room temperature under atomospheric pressure of hydrogen gas
  9. customAfter hydrogen absorption
  10. filtrationthe catalyst is filtered off
  11. concentrationthe filtrate is concentrated under reduced pressure
  12. additionTo the residue are added dioxane (30 ml), concentrated hydrochloric acid (2 ml) and water (10 ml)
  13. waitthe mixture is left
  14. waitstanding at room temperature for one hour
  15. concentrationThe resultant is concentrated under reduced pressure
  16. additionThe precipitating crystals are treated with water (10 ml)
  17. filtrationcollected by filtration

Sources & evidence

ORD record
ord-234b0cde01034c77a056984768d0658c
Source dataset
uspto-grants-1989_11
Patent number
US04880809

Reaction notes

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