Ethanol → HCID 12051800, compound

HRID 1756415Notes

Reaction equation

HRID 1756415 reaction equation
[CH3:1][C:2]1([CH3:21])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14](=[O:20])[C:15]([O:17]CC)=[O:16])[CH:5]=[CH:4][C:3]1=2.C(O)C.[OH-].[Na+]>O>[CH3:1][C:2]1([CH3:21])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14](=[O:20])[C:15]([OH:17])=[O:16])[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 21267561HCID 21267561, compound

Product 1

HCID 12051800HCID 12051800, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

16 g (55.6 mmol) of the ester obtained above in (a) and 50 ml of ethyl alcohol are introduced into a round-bottomed flask. A solution of 2.5 g (58.5 mmol) of sodium hydroxide in 50 ml of water is added and the mixture is heated to reflux for one hour. The reaction medium is evaporated to dryness, the residue is taken up with water, the mixture is extracted with ethyl ether, the aqueous phase is separated after settling has taken place, acidified to pH 1 with concentrated hydrochloric acid and extracted with ethyl ether, and the organic phase is separated after settling has taken place, dried over magnesium sulphate and evaporated. 14 g (97%) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylglyoxylic acid are collected in the form of a colorless oil.

Workup

  1. additionare introduced into a round-bottomed flask
  2. temperaturethe mixture is heated
  3. temperatureto reflux for one hour
  4. customThe reaction medium is evaporated to dryness
  5. extractionthe mixture is extracted with ethyl ether
  6. customthe aqueous phase is separated after settling
  7. extractionextracted with ethyl ether
  8. customthe organic phase is separated after settling
  9. dry with materialdried over magnesium sulphate
  10. customevaporated
  11. custom14 g (97%) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylglyoxylic acid are collected in the form of a colorless oil

Sources & evidence

ORD record
ord-4041036a7d51441fa2ecf2e436c76a29
Source dataset
uspto-grants-1995_08
Patent number
US05439925

Reaction notes

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