Water → HCID 13046224, compound

HRID 1759459Notes

Reaction equation

HRID 1759459 reaction equation
Br[CH2:2]/[CH:3]=[C:4](\[CH3:12])/[CH:5]([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8].[C:13]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)(=[O:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:13]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:2]/[CH:3]=[C:4](\[CH3:12])/[CH:5]([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8])=[CH:19][CH:18]=1)(=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 1983AcetaminophenHCID 11430Potassium CarbonateHCID 13046223HCID 13046223, compound

Product 1

HCID 13046224HCID 13046224, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.0 g (E)-4-bromo-1,1-diethoxy-2-methyl-2-butene in 10 ml of sieve dried dimethyl formamide is treated with 0.7 g of p-acetylaminophenol and 0.64 g anhydrous potassium carbonate. The suspension is stirred under nitrogen for four days and the mixture is then poured into 100 ml water and the hazy solution extracted with two 100 ml portions of benzene. The benzene extract is washed with water and dried with sodium sulfate. The benzene extract is concentrated and vacuum dried to give 0.75 g of (E)-4-(4-acetylaminophenoxy)-1,1-diethoxy-2-methyl-2-butene which is dissolved in about 5 to 10 ml acetone and treated with about 1 ml water and a spatula of p-toluenesulfonic acid monohydrate. The resulting solution is agitated occasionally for 30 minutes and the solution is evaporated at room temperature giving a solid, ethylether insoluble residue. The residue is dissolved in about 150 ml methylene chloride and washed twice with water. The residue is dried with sodium sulfate and concentration gave 0.45 g of a solid. The material is filtered in about 50 ml of hot carbon tetrachloride-benzene then boiled down to about 10 ml. The product is filtered and washed with room temperature carbon tetrachloride giving 0.2 g white solid, m.p. 127°-30° C. Elemental Analysis. Calculated for C13H15NO3 : C,66.94; H,6.48; N,6.00. Found: C,66.64; H,6.29; N,5.75.

Workup

  1. extractionthe hazy solution extracted with two 100 ml portions of benzene
  2. extractionThe benzene extract
  3. washis washed with water
  4. dry with materialdried with sodium sulfate
  5. extractionThe benzene extract
  6. concentrationis concentrated
  7. customvacuum dried

Sources & evidence

ORD record
ord-c08c9e28248545938b619e1646502d19
Source dataset
uspto-grants-1982_07
Patent number
US04340765

Reaction notes

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