Sulfuric Acid → Agn-190205

HRID 1657133Notes

Reaction equation

HRID 1657133 reaction equation
Cl[CH:2](P(=O)(OCC)OCC)[C:3]1[CH:12]=[CH:11][C:10]2[C:9]([CH3:14])([CH3:13])[CH2:8][CH2:7][C:6]([CH3:16])([CH3:15])[C:5]=2[CH:4]=1.[C:25]([C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1)([OH:27])=[O:26].S(=O)(=O)(O)O>CS(C)=O>[CH3:13][C:9]1([CH3:14])[CH2:8][CH2:7][C:6]([CH3:16])([CH3:15])[C:5]2[CH:4]=[C:3]([C:2]#[C:32][C:31]3[CH:34]=[CH:35][C:28]([C:25]([OH:27])=[O:26])=[CH:29][CH:30]=3)[CH:12]=[CH:11][C:10]1=2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 120884-Formylbenzoic acidHCID 13604831Diethyl 1-chloro-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)methylphosphonate

Product 1

HCID 10314719Agn-190205Yield 70.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

22.6 g (0.06 mole) of diethyl 1-chloro-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-methylphosphonate (about 85% strength) and 9 g of 4-carboxybenzaldehyde in 190 ml of dry dimethyl sulfoxide were initially taken. 21 g (0.185 mole) of potassium tert.-butylate in 5 ml of dimethyl sulfoxide were added dropwise to the stirred mixture at room temperature. Stirring was continued for 1 hour, after which the reaction mixture was poured onto 1 liter of ice water and acidified with 20% strength sulfuric acid. The resulting precipitate was filtered off under suction, washed with water and recrystallized from isopropanol to give 14 g (70%) of the title compound. Carrying out recrystallization twice more gave 6 g of pure material of melting point 263°-264° C.

Workup

  1. filtrationThe resulting precipitate was filtered off under suction
  2. washwashed with water
  3. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-5ef363ece53b4909adc7db3f81ae2794
Source dataset
uspto-grants-1993_10
Patent number
US05256694

Reaction notes

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