Phosphoric Acid → 7-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-7-phenylheptane

HRID 1464522

Reaction equation

HRID 1464522 reaction equation
C([Li])CCC.[CH2:6]([C:13]1[C:18]([CH3:19])=[C:17]([O:20][CH3:21])[C:16]([CH3:22])=[C:15]([CH3:23])[C:14]=1[O:24][CH3:25])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CC(C)(N)C(C)(C)N.[CH2:34](Br)[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39].P(=O)(O)(O)O>O1CCCC1.CCCCCC>[CH3:25][O:24][C:14]1[C:15]([CH3:23])=[C:16]([CH3:22])[C:17]([O:20][CH3:21])=[C:18]([CH3:19])[C:13]=1[CH:6]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Participants

8

Reactant 5

HCID 1004Phosphoric AcidHCID 81011-BromohexaneHCID 1233902,3-Butanediamione, 2,3-dimethyl-HCID 190880201-Benzyl-2,5-dimethoxy-3,4,6-trimethylbenzeneHCID 178418339Butyllithium

Product 1

HCID 190880827-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-7-phenylheptaneYield 77%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A 3.1 ml (5.0 mmole) portion of n-butyllithium.hexane solution was added dropwise to 1.35 g (5.0 mmole) of 1-benzyl-2,5-dimethoxy-3,4,6-trimethylbenzene and 0.83 ml (5×1.1 mmole) of 1,1,2,2-tetramethylethylenediamine dissolved in anhydrous tetrahydrofuran (15 ml), under an atmosphere of argon at 50° C. over the period of 5 minutes, followed by stirring at 50° to 55° C. for 25 minutes. Then, a solution of 0.83 (5.0 mmole) of n-hexyl bromide in tetrahydrofuran (5 ml) was added dropwise to the mixed solution over the period of 5 minutes, followed by stirring at 50° C. for further 10 minutes. The reaction solution was cooled with ice and made acid by adding a 10% aqueous phosphoric acid solution, and the product was extracted with isopropyl ether. The organic layer was separated out, washed with aqueous sodium chloride solution, dried (magnesium sulfate) and evaporated. The residual solution was chromatographed on a silica gel column to effect purification (elution with hexane/isopropyl ether) to thereby give 1.37 g (77%) of 7-(2,5-dimethoxy-3,4,6-trimethylphenyl)-7-phenylheptane. Its typical physical properties and nuclear magnetic resonance specrum data are shown in Table 14.

Workup

  1. stirringby stirring at 50° C. for further 10 minutes
  2. temperatureThe reaction solution was cooled with ice
  3. extractionthe product was extracted with isopropyl ether
  4. customThe organic layer was separated out
  5. washwashed with aqueous sodium chloride solution
  6. dry with materialdried (magnesium sulfate)
  7. customevaporated
  8. customThe residual solution was chromatographed on a silica gel column to effect purification (elution with hexane/isopropyl ether)

Sources & evidence

ORD record
ord-be66aef433ea4838aa4ef1014b7dc05c
Source dataset
uspto-grants-1994_04
Patent number
US05304658

Linked notes

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