Hydrochloric Acid → Ethyl 4-formylcyclohexane-1-carboxylate

HRID 565153

Reaction equation

HRID 565153 reaction equation
[CH2:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.[Cl-].[CH3:13][O:14]C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].Cl>C(OC)(C)(C)C.O1CCCC1.O>[CH:13]([CH:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1)=[O:14]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 18686Ethyl cyclohexanoateHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 13548164Ethyl 4-formylcyclohexane-1-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

Under a nitrogen atmosphere, 425.5 g of ethyl 4-cyclohexanecarboxylate and 856.7 g of methoxymethyltriphenylphosphonium chloride were suspended in 2.2 l of methyl tert-butyl ether. A solution of 280.4 g of potassium tert-butoxide in 400 ml of tetrahydrofuran was then added dropwise to the stirred suspension. The suspension was then stirred overnight at RT, and the next day 430 ml of 10% hydrochloric acid were added and the mixture was warmed at 55° C. for 1 hour. 50 ml of water were then added to the suspension. Conventional work-up gave ethyl 4-formylcyclohexanecarboxylate.

Workup

  1. temperaturethe mixture was warmed at 55° C. for 1 hour

Sources & evidence

ORD record
ord-2fbd981f82d742268fc37b159a31a054
Source dataset
uspto-grants-2001_01
Patent number
US06171664B2

Linked notes

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