Ethanol → HCID 14100567, compound

HRID 1198894Notes

Reaction equation

HRID 1198894 reaction equation
[CH3:1][C:2]1([CH3:25])[C:10]2[C:5](=[CH:6][C:7]([C:11]([C:13]3[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=3[C:15]([OH:17])=[O:16])=[O:12])=[CH:8][CH:9]=2)[C:4]([CH3:23])([CH3:22])[CH:3]1[CH3:24].S(=O)(=O)(O)O.[CH2:31](O)[CH3:32]>>[CH3:1][C:2]1([CH3:25])[C:10]2[C:5](=[CH:6][C:7]([C:11]([C:13]3[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=3[C:15]([O:17][CH2:31][CH3:32])=[O:16])=[O:12])=[CH:8][CH:9]=2)[C:4]([CH3:23])([CH3:22])[CH:3]1[CH3:24]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 14100565HCID 14100565, compound

Product 1

HCID 14100567HCID 14100567, compound

Procedure

A solution of 2.4 g (7.1 mmoles) of 2-[(1,1,2,3,3-pentamethyl-5-indanyl)carbonyl]benzoic acid, described in Example II, in 80 cm3 of ethyl alcohol containing 0.1 cm3 of 98% sulfuric acid, is heated for 12 hours at reflux. The solution is then concentrated under reduced pressure. The crude ester is dissolved in 100 cm3 of ethyl ether. The etherified solution is washed with sodium bicarbonate and then with water, dried on sodium sulfate and finally evaporated to dryness. After drying, 2.5 g of ethyl 2-[(1,1,2,3,3-pentamethyl-5-indanyl)carbonyl]benzoate in the form of a colorless oil are obtained which slowly crystallizes at ambient temperature to give a white solid whose melting point is 56-57° C. The NMR1H 80 MHz and IR spectra conform to the expected structure.

Workup

  1. temperatureis heated for 12 hours
  2. temperatureat reflux
  3. concentrationThe solution is then concentrated under reduced pressure
  4. dissolutionThe crude ester is dissolved in 100 cm3 of ethyl ether
  5. washThe etherified solution is washed with sodium bicarbonate
  6. dry with materialwith water, dried on sodium sulfate
  7. customfinally evaporated to dryness
  8. customAfter drying

Sources & evidence

ORD record
ord-86ca96e904764a969356a75a204ec9b3
Source dataset
uspto-grants-1990_02
Patent number
US04898864

Reaction notes

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