O-Cresol → Diethyl 2-(2-methylphenoxy)pentanedioate

HRID 2073537Notes

Reaction equation

HRID 2073537 reaction equation
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH:10]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:11]([O:13][CH2:14][CH3:15])=[O:12].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[C:18]([CH:17]([O:7][C:6]1[CH:5]=[CH:4][CH:3]=[CH:2][C:1]=1[CH3:8])[CH2:16][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])([O:20][CH2:21][CH3:22])=[O:19]

Participants

6

Reactant 4

HCID 335O-CresolHCID 962WaterHCID 11430Potassium CarbonateHCID 522444Pentanedioic acid, 2-bromo-, diethyl ester

Product 1

HCID 14774131Diethyl 2-(2-methylphenoxy)pentanedioate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of o-cresol (0.1 mol) and diethyl 2-bromoglutarate (0.1 mol) and K2CO3 (0.11 mol) in 50 mL of DMF are heated at 70° C. overnight. The reaction is poured into water and extracted with ethyl acetate. The organic solution is washed with water, 0.1N NaOH solution, dried and evaporated to give ethyl 4-carbethoxy-4-(2-methylphenoxy)butyrate which is used directly in the next step.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic solution is washed with water, 0.1N NaOH solution
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-988df70dcf244307bd166e9ace6ac173
Source dataset
uspto-grants-1990_04
Patent number
US04918081

Reaction notes

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