Cyclohexanecarboxylic acid → 1-(Methoxymethyl)cyclohexanecarboxylic acid

HRID 894358Notes

Reaction equation

HRID 894358 reaction equation
[CH:1]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([N-]C(C)C)(C)C.[Li+].C([Li])CCC.C(NC(C)C)(C)C.[CH3:30][O:31][CH2:32]Cl>CCCCCC.C1COCC1>[CH3:30][O:31][CH2:32][C:1]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 7413Cyclohexanecarboxylic acidHCID 7864Chloromethyl Methyl EtherHCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 178418339Butyllithium

Product 1

HCID 184057031-(Methoxymethyl)cyclohexanecarboxylic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
60 °C

Procedure

11.8 g (0.093 mole) of cyclohexylcarboxylic acid were added to a solution of lithium diisopropylamide prepared using 125 cm3 of a 1.50 M solution of butyllithium in hexane, 18.9 g of diisopropylamine and 200 cm3 of THF as the starting materials. After the mixture had been heated at 60° C. for 2 hours, 8 g of methoxymethyl chloride were added, at a temperature of -30° C. After the customary treatment, methoxymethylcyclohexylcarboxylic acid was distilled; this was in the form of a colourless liquid which crystallised on cooling.

Workup

  1. customprepared
  2. distillationAfter the customary treatment, methoxymethylcyclohexylcarboxylic acid was distilled
  3. customcrystallised
  4. temperatureon cooling

Sources & evidence

ORD record
ord-60e3f412bda94702a6dde96d5d4dc918
Source dataset
uspto-grants-1981_08
Patent number
US04283420

Reaction notes

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