Ethanol → HCID 12051800, compound

HRID 565148Notes

Reaction equation

HRID 565148 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 ethyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylglyoxylate and 50 ml of ethyl alcohol were introduced into a round-bottomed flask. A solution of 2.5 g (58.5 mmol) of sodium hydroxide in 50 ml of water was added and the mixture was heated at reflux for one hour. The reaction medium was evaporated to dryness, taken up in water and ethyl ether, the aqueous phase decanted off, acidified to pH 1 with concentrated hydrochloric acid, extracted with ethyl ether, the organic phase decanted off, dried over magnesium sulfate and evaporated. 14 g (97%) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylglyoxylic acid were recovered in the form of a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for one hour
  3. customThe reaction medium was evaporated to dryness
  4. customethyl ether, the aqueous phase decanted off
  5. extractionextracted with ethyl ether
  6. customthe organic phase decanted off
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. custom14 g (97%) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylglyoxylic acid were recovered in the form of a colorless oil

Sources & evidence

ORD record
ord-72163de948414c02b57ad053c7ad1b97
Source dataset
uspto-grants-2001_01
Patent number
US06171603B2

Reaction notes

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