Potassium Hydroxide → 2-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)acetic acid

HRID 2294537Notes

Reaction equation

HRID 2294537 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14](=O)[C:15]([OH:17])=[O:16])[CH:5]=[CH:4][C:3]1=2.[OH-].[K+]>O.NN>[CH3:1][C:2]1([CH3:19])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([CH2:14][C:15]([OH:17])=[O:16])[CH:5]=[CH:4][C:3]1=2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 12051800HCID 12051800, compound

Product 1

HCID 181779322-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 24654Hydrazine hydrate (1:1)Solvent

Procedure

4.68 g (18 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylglyoxylic acid and 50 ml of hydrazine hydrate are introduced into a round-bottomed flask and the mixture is heated to reflux until dissolution has taken place. At 100° C., 8 g of potassium hydroxide are added in small portions and the mixture is heated to reflux for four hours. The reaction medium is evaporated to dryness, the residue is taken up with water, the mixture is acidified to pH 1 with concentrated hydrochloric acid and extracted with ethyl ether, and the organic phase is separated after settling has taken place, then dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a silica column and eluted with a mixture of dichloromethane and ethyl ether (95:5). After evaporation of the solvents, 3.8 g (86%) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylacetic acid, melting point 149°-150° C., are collected.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux until dissolution
  3. temperaturethe mixture is heated
  4. temperatureto reflux for four hours
  5. customThe reaction medium is evaporated to dryness
  6. extractionextracted with ethyl ether
  7. customthe organic phase is separated after settling
  8. dry with materialdried over magnesium sulphate
  9. customevaporated
  10. customThe residue obtained
  11. customis purified by chromatography on a silica column
  12. washeluted with a mixture of dichloromethane and ethyl ether (95:5)
  13. customAfter evaporation of the solvents, 3.8 g (86%) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylacetic acid, melting point 149°-150° C.
  14. customare collected

Sources & evidence

ORD record
ord-df75854ba6cd4d57b1732a4d0f7a036a
Source dataset
uspto-grants-1997_11
Patent number
US05688817

Reaction notes

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