Phenylacetic Acid → HCID 19884920, compound

HRID 846195Notes

Reaction equation

HRID 846195 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(P(N(C)C)(N(C)C)=O)C.C([Li])CCC.[CH3:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([O:38][CH2:39][CH2:40]Cl)=[CH:30][CH:29]=1>C1COCC1.O>[C:8]([CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:40][CH2:39][O:38][C:31]1[C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:28]([CH3:27])=[CH:29][CH:30]=1)([OH:10])=[O:9]

Participants

7

Reactant 4

HCID 999Phenylacetic AcidHCID 12679HexamethylphosphoramideHCID 19884894HCID 19884894, compoundHCID 178418339Butyllithium

Product 1

HCID 19884920HCID 19884920, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 1 1. three-neck round bottom flask fitted with a thermometer, nitrogen inlet tube, addition funnel and magnetic stirrer was added 5.9 g (43.6 mmol) of phenylacetic acid and 250 ml of tetrahydrofuran. To the mixture was added 7.6 ml (43.6 mmol) of HMPA. The mixture was cooled to approximately 0° C. and 6.4 ml (89.4 mmol) of 1.48M n-butyllithium was added dropwise to the reaction mixture. The mixture was warmed to room temperature over a period of approximately 50 minutes and cooled to approximately -78° C. To the reaction mixture was added a solution of 2-(4-methyl-1-naphthalenyloxy)ethyl chloride dissolved in 100 ml of THF. The reaction mixture was stirred at room temperature overnight and diluted with water. The mixture was washed twice with diethyl ether and the resulting aqueous phase was acidified. The aqueous phase was extracted twice with diethyl ether and the organic extracts were combined, washed twice with water, once with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The volatile constituents were evaporated under vacuum to provide 9.53 g of a light tan solid. The solid was recrystallized from diethyl ether and hexane to provide 5.62 g of the desired product. mp=130°-131.5° C.

Workup

  1. customthree-neck round bottom flask fitted with a thermometer, nitrogen inlet tube, addition funnel and magnetic stirrer
  2. temperatureThe mixture was warmed to room temperature over a period of approximately 50 minutes
  3. temperaturecooled to approximately -78° C
  4. washThe mixture was washed twice with diethyl ether
  5. extractionThe aqueous phase was extracted twice with diethyl ether
  6. washwashed twice with water, once with a saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe volatile constituents were evaporated under vacuum

Sources & evidence

ORD record
ord-fb4ef539877643aea0549e3384d61f4c
Source dataset
uspto-grants-1992_08
Patent number
US05135947

Reaction notes

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