Methanol → Pentanedioic acid, 2,4-dimethyl-, monomethyl ester

HRID 1633265Notes

Reaction equation

HRID 1633265 reaction equation
[C:1](CC(C)C(Cl)=O)(OC)=[O:2].[CH3:11][CH:12]1[CH2:18][CH2:17][C:16](=O)[O:15][C:13]1=[O:14].C(CCC(C)C(Cl)=O)(OC)=O.CC1CC(=O)OC(=O)C1.[CH3:40][OH:41]>>[C:40]([CH:17]([CH3:16])[CH2:18][CH:12]([CH3:11])[C:13]([OH:15])=[O:14])([O:2][CH3:1])=[O:41]

Participants

6

Reactant 5

HCID 887MethanolHCID 778283-Methylglutaric anhydrideHCID 3015571dihydro-3-methyl-2H-pyran-2,6(3H)-dioneHCID 13192898Methyl 5-chloro-4-methyl-5-oxopentanoateHCID 14403282Methyl 4-chloro-3-methyl-4-oxobutanoate

Product 1

HCID 549975Pentanedioic acid, 2,4-dimethyl-, monomethyl ester

Procedure

The starting materials for said compounds 1, 2, 4, 6, 11 and 12 are the 3-carbomethoxy-2-methylpropanoyl chloride, 2-methylglutaric anhydride, 4-carbomethoxy-2-methylbutanoyl chloride, 3-methylglutaric anhydride and the erythro or threo 4-carbomethoxy-4-(2-phenethyl)-2-methylbutanoyl chloride respectively. That of compound 8 and 9 may be prepared as follows: The solution of 6.0 of meso-2,4-dimethylglutaric acid anhydride [J. Am. Chem. Soc. 77, 1862 (1955)] in 4 ml of methanol is refluxed for one hour and evaporated, to yield the erythro 4-carbomethoxy-2,4-dimethylbutanoic acid. It is converted into the acid chloride by refluxing it with 10.9 g of oxalyl chloride in 50 ml of methylene chloride for 2 hours, and evaporating said mixture.

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-6c1697f0a648407e8ce97bd6d40d4f9f
Source dataset
uspto-grants-1984_10
Patent number
US04479963

Reaction notes

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