Ethanol → HCID 72722442, compound

HRID 1479167Notes

Reaction equation

HRID 1479167 reaction equation
[CH3:1][C:2]1([CH3:29])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([S:14]([CH2:17][CH2:18][C:19]3[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[CH:21][CH:20]=3)(=[O:16])=[O:15])[CH:5]=[CH:4][C:3]1=2.C(O)C.O>O1CCCC1>[CH3:1][C:2]1([CH3:29])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([S:14]([CH2:17][CH2:18][C:19]3[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:27][CH:28]=3)(=[O:16])=[O:15])[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 3

HCID 702EthanolHCID 962WaterHCID 90078497HCID 90078497, compound

Product 1

HCID 72722442HCID 72722442, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The methyl 4-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-sulphonyl)-ethyl]benzoate (3.54, 8.54 mmol) is placed in solution in 256 ml of tetrahydrofuran, 25.6 ml of ethanol and 12.8 ml of water in a round-bottomed flask. 3.54 g of lithia monohydrate are added. The whole mixture is stirred for 4 hours at reflux. Ambient the reaction medium is concentrated by half, taken up with ethyl acetate and water and then brought to pH6 with 2N HCl. After extraction, the organic phase is washed with a saturated NaCl solution, dried over MgSO4, concentrated and washed with ether. 3 g of 4-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-sulphonyl)ethyl]benzoic acid are obtained in the form of a white solid.

Workup

  1. temperatureat reflux
  2. concentrationAmbient the reaction medium is concentrated by half
  3. extractionAfter extraction
  4. washthe organic phase is washed with a saturated NaCl solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. washwashed with ether

Sources & evidence

ORD record
ord-a22572ae5e894ac195c3d547c0547440
Source dataset
uspto-grants-2016_08
Patent number
US09408793B2

Reaction notes

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