O-Xylene → Methyl 1-methylcyclopropane-1-carboxylate

HRID 1267683Notes

Reaction equation

HRID 1267683 reaction equation
C1(C)C(C)=CC=CC=1.[Cl:9][CH2:10][CH2:11][CH:12]([CH3:17])[C:13]([O:15][CH3:16])=[O:14].C[O-].[Na+]>CO>[CH3:17][C:12]1([C:13]([O:15][CH3:16])=[O:14])[CH2:10][CH2:11]1.[Cl:9][CH2:10][CH2:11][CH:12]([CH3:17])[C:13]([O:15][CH3:16])=[O:14]

Participants

6

Reactant 3

HCID 7237O-XyleneHCID 10942334Sodium MethoxideHCID 11263584Methyl 4-Chloro-2-methylbutyrate

Product 2

HCID 543995Methyl 1-methylcyclopropane-1-carboxylateHCID 11263584Methyl 4-Chloro-2-methylbutyrate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

contacting the xylene solution of methyl 4-chloro-2-methylbutyrate from step (3) with an sodium methoxide and heating at temperatures of about 100 to 200° C. which causes vaporization of (i) methanol as it is formed and (ii) methyl 1-methylcyclopropanecarboxylate as it is formed from methyl 4-chloro-2-methylbutyrate.

Workup

  1. customis formed

Sources & evidence

ORD record
ord-06594cb39e2b46899741b890488f1755
Source dataset
uspto-grants-2003_04
Patent number
US06552217B2

Reaction notes

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