Hexane → Ethyl 5-Hydroxy-4-methyl-7-(1-methyl-4-phenylbutyl)coumarin-3-propionate

HRID 1389184

Reaction equation

HRID 1389184 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:10])[CH:5]=[C:6]([OH:8])[CH:7]=1.[CH3:20][CH2:21][O:22][C:23]([CH2:25][CH2:26][CH:27]([C:31](OCC)=[O:32])[C:28]([CH3:30])=O)=[O:24].P(Cl)(Cl)(Cl)=O.CCCCCC>C(Cl)(Cl)Cl>[OH:1][C:2]1[CH:3]=[C:4]([CH:9]([CH3:10])[CH2:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:5]=[C:6]2[C:7]=1[C:28]([CH3:30])=[C:27]([CH2:26][CH2:25][C:23]([O:22][CH2:21][CH3:20])=[O:24])[C:31](=[O:32])[O:8]2

Participants

6

Reactant 4

HCID 8058HexaneHCID 24813Phosphorus oxychlorideHCID 73915Diethyl 2-acetylglutarateHCID 204873675-(5-Phenylpentan-2-yl)benzene-1,3-diol

Product 1

HCID 53719146Ethyl 5-Hydroxy-4-methyl-7-(1-methyl-4-phenylbutyl)coumarin-3-propionate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 2-(3,5-dihydroxyphenyl)-5-phenylpentane (33 g., 0.13 M), (Preparation C) diethyl α-acetoglutarate (32.2 g., 0.14 M) and phosphorous oxychloride (20 g., 0.13 M), protected from atmospheric moisture, is stirred at room temperature. After 10 days, the mixture is dissolved in chloroform, washed three times with water, dried (Na2SO4), and evaporated. The residue is subjected to silica gel chromatography (eluents--9 benzene:1 ether) to yield 22 g. of the desired ester, m.p. 58°-70° C. from hexane. Further recrystallization from ethyl acetate/hexane affords an analytical sample: m.p. 78°-85° C.

Workup

  1. washwashed three times with water
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customto yield 22 g
  5. customFurther recrystallization from ethyl acetate/hexane
  6. customaffords an analytical sample

Sources & evidence

ORD record
ord-0decae391ec24e7f9a84a79f28035cc6
Source dataset
uspto-grants-1981_01
Patent number
US04243674

Linked notes

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