Formaldehyde → 2-Propyl-pentanoic acid chloromethyl ester

HRID 852470Notes

Reaction equation

HRID 852470 reaction equation
C=[O:2].[CH2:3]([CH:6]([CH2:10][CH2:11][CH3:12])[C:7](Cl)=[O:8])[CH2:4][CH3:5].[CH2:13]([Cl:15])Cl>[Cl-].[Zn+2].[Cl-]>[Cl:15][CH2:13][O:8][C:7](=[O:2])[CH:6]([CH2:10][CH2:11][CH3:12])[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6344DichloromethaneHCID 762402-Propylvaleryl chloride

Product 1

HCID 128400662-Propyl-pentanoic acid chloromethyl esterYield 58%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

Para-formaldehyde (1 g) and zinc chloride (catalytic amount) were mixed together at 0° C. 2,2-Di-n-propylacetyl chloride (30 mole, 4.88 g) was added dropwise over 1 hour. The reaction was warmed to ambient temperature, then was heated to 50-55° C. for 6 hours. The reaction mixture continued stirring at room temperature for 16 hours. The reaction mixture was taken up with methylene chloride (5 mL) and flash chromatographed on 150 g silica gel. Elution with 1 to 5% ethyl acetate/hexane gave 3.3 g (58%) of the desired product.

Workup

  1. temperaturewas heated to 50-55° C. for 6 hours
  2. customchromatographed on 150 g silica gel
  3. washElution with 1 to 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-df82ab4edbb14b3a98b02531031427ba
Source dataset
uspto-grants-2007_08
Patent number
US07253153B2

Reaction notes

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