Ethyl orthoformate → Diethyl 4,4-diethoxyheptanedioate

HRID 570646Notes

Reaction equation

HRID 570646 reaction equation
C(OCC)(OCC)[O:2][CH2:3][CH3:4].[O:11]=[C:12]([CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].O.[C:28]1(C)C=CC(S(O)(=O)=O)=C[CH:29]=1>CCO>[CH2:28]([O:11][C:12]([O:2][CH2:3][CH3:4])([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH3:29]

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 80592Diethyl 4-oxoheptanedioateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 59487222Diethyl 4,4-diethoxyheptanedioate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
77 °C

Procedure

To EtOH (27.8 L), triethyl orthoformate (9.26 L, 55.6 mol) and diethyl 4-oxopimelate (5.93 L, 27.8 mol) was added p-toluenesulfonic acid monohydrate (0.053 kg, 0.278 mol), and the reaction mixture was heated to 77.0° C. with stirring for 20 h. Heating was discontinued, and ethanol was removed by distillation under vacuum, starting with the batch at 63° C. The remaining orange ketal solution was dissolved in toluene (32 L) and transferred to a 100-L extractor that had been charged with 2% NaHCO3 (24 L), with stirring.

Workup

  1. temperatureHeating
  2. customethanol was removed by distillation under vacuum
  3. customstarting with the batch at 63° C
  4. dissolutionThe remaining orange ketal solution was dissolved in toluene (32 L)
  5. additionhad been charged with 2% NaHCO3 (24 L)
  6. stirringwith stirring

Sources & evidence

ORD record
ord-ddff9273848d4d03932fcee852a5837b
Source dataset
uspto-grants-2015_05
Patent number
US09023864B2

Reaction notes

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