Sodium Carbonate → HCID 23090642, compound

HRID 1787958Notes

Reaction equation

HRID 1787958 reaction equation
[Cl:1][CH2:2][CH2:3][CH:4](C)[CH:5]=O.[CH:8]([O:15][CH2:16][CH3:17])([O:12][CH2:13][CH3:14])OCC.C([O-])([O-])=O.[Na+].[Na+]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)C>[CH2:16]([O:15][CH:8]([O:12][CH2:13][CH3:14])[CH:4]([CH3:5])[CH2:3][CH2:2][Cl:1])[CH3:17]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 31214Ethyl orthoformateHCID 113893844-chloro-2-methylbutyraldehyde

Product 1

HCID 23090642HCID 23090642, compoundYield 41.1%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 4-chloro-2-methylbutyraldehyde (4.8 g, 0.040 moles), triethyl orthoformate (6.48 g, 0.044 moles), ethyl alcohol (3.0 g), and p-toluenesulfonic acid monohydrate (0.0144 g, 0.000757 moles) was stirred at 45° C. overnight under an argon atmosphere. Next, after cooling to room temperature, Na2CO3 (0.40 g) was added and the mixture was stirred for 15 min. The reaction mixture was filtered and ethyl alcohol and residual triethyl orthoformate were distilled off under reduced pressure. The residue was subjected to fractional vacuum distillation giving 3.2 g of pure 4-chloro-2-methylbutyraldehyde diethyl acetal.

Workup

  1. temperatureNext, after cooling to room temperature
  2. stirringthe mixture was stirred for 15 min
  3. filtrationThe reaction mixture was filtered
  4. distillationethyl alcohol and residual triethyl orthoformate were distilled off under reduced pressure
  5. distillationThe residue was subjected to fractional vacuum distillation

Sources & evidence

ORD record
ord-9e41983dcaff4233809d182e77ca4890
Source dataset
uspto-grants-2009_03
Patent number
US07511094B2

Reaction notes

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