Ethanol → HCID 14100562, compound

HRID 1198898Notes

Reaction equation

HRID 1198898 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]([C:16]3[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=3[C:18]([OH:20])=[O:19])=[O:15])[CH:5]=[CH:4][C:3]1=2.S(=O)(=O)(O)O.[CH2:31](O)[CH3:32]>>[CH3:1][C:2]1([CH3:25])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]([C:16]3[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=3[C:18]([O:20][CH2:31][CH3:32])=[O:19])=[O:15])[CH:5]=[CH:4][C:3]1=2

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 9905799HCID 9905799, compound

Product 1

HCID 14100562HCID 14100562, compound

Procedure

A solution of 8.41 g (0.025 mole) of 2-[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) carbonyl]benzoic acid, described in Example I, in 300 cm3 of ethyl alcohol containing 0.4cm3 of 98% sulfuric acid is heated for 14 hours at reflux. The solution is then concentrated under reduced pressure and the resulting crude ester is dissolved in 300 cm3 of ethyl ether. The ether solution is washed with sodium bicarbonate and then with water, dried on sodium sulfate and evaporated to dryness. After drying, 7.9 g of ethyl 2-[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) carbonyl]benzoate are obtained in the form of a colorless oil which slowly crystallizes at ambient temperature to give a white solid whose melting point is 58°-59° C.

Workup

  1. temperatureis heated for 14 hours
  2. temperatureat reflux
  3. concentrationThe solution is then concentrated under reduced pressure
  4. dissolutionthe resulting crude ester is dissolved in 300 cm3 of ethyl ether
  5. washThe ether solution is washed with sodium bicarbonate
  6. dry with materialwith water, dried on sodium sulfate
  7. customevaporated to dryness
  8. customAfter drying

Sources & evidence

ORD record
ord-0aa77301de7842aab389ba662c3b23dd
Source dataset
uspto-grants-1990_02
Patent number
US04898864

Reaction notes

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