Ethanol → Diethyl 2-phenylbutanedioate

HRID 2415022Notes

Reaction equation

HRID 2415022 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH:7]([C:12]([OH:14])=[O:13])[CH2:8][C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.[CH2:15](O)[CH3:16].[C:18]1(C)C=CC=C[CH:19]=1.OS(O)(=O)=O>O>[C:4]1([CH:7]([CH2:8][C:9]([O:11][CH2:15][CH3:16])=[O:10])[C:12]([O:14][CH2:18][CH3:19])=[O:13])[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 1118Sulfuric AcidHCID 1140Toluene2×HCID 95459Phenylsuccinic acid

Product 1

HCID 249294Diethyl 2-phenylbutanedioate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 50 g of DL-phenylsuccinic acid (0.257 mol), 90 mL (1.59 mol) of ethanol, 46 mL of toluene and 0.39 g of concentrated H2SO4 was heated to 115° C. An azeotropic mixture of ethanol, toluene and water was distilled over a column of 10 cm. When the distillation stopped the same amounts of ethanol and toluene was added. To obtain a complete conversion this was repeated twice. The resulting oil was distilled at 114° C. (2·10−2 mbar); yield 60.82 g (95%), purity 100%

Workup

  1. distillationwas distilled over a column of 10 cm
  2. distillationWhen the distillation
  3. additionwas added
  4. customTo obtain a complete conversion
  5. distillationThe resulting oil was distilled at 114° C. (2·10−2 mbar)

Sources & evidence

ORD record
ord-d787d16433df40e29c85594919a8f053
Source dataset
uspto-grants-2004_11
Patent number
US06818583B1

Reaction notes

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