ChemicalBook CAS DataBase List (1r,4r)-methyl 4-formylcyclohexanecarboxylate

(1r,4r)-methyl 4-formylcyclohexanecarboxylate synthesis

7synthesis methods

Product Name:(1r,4r)-methyl 4-formylcyclohexanecarboxylate
CAS Number:54274-80-5
Molecular formula:C9H14O3
Molecular Weight:170.21

110928-44-4 Synthesis

(1r,4r)-methyl 4-(hydroxymethyl)cyclohexanecarboxylate

110928-44-4
102 suppliers
$19.00/100mg

(1r,4r)-methyl 4-formylcyclohexanecarboxylate

54274-80-5
91 suppliers
$30.00/1g

Yield:54274-80-5 100%

Reaction Conditions:

Stage #1:trans-(4-hydroxymethyl)cyclohexane-1-carboxylic acid methyl ester with oxalyl dichloride;dimethyl sulfoxide in dichloromethane at -65; for 0.5 h;
Stage #2: with triethylamine in dichloromethane at -65; for 0.25 h;

Steps:

trans-4-Formyl-cyclohexanecarboxylic acid methyl ester
trans-4-Formyl-cyclohexanecarboxylic acid methyl ester
To a solution of dimethylsulfoxide (9.53 g, 122 mmol) in dry dichloromethane (400 ml) was slowly added oxalyl chloride (7.74 g, 61.0 mmol) at -78° C.
The cooling bath was removed and the reaction mixture was stirred at -50° C. for 5 min.
A solution of trans-4-hydroxymethyl-cyclohexanecarboxylic acid methyl ester (8.75 g, 50.8 mmol) in dichloromethane (108 ml) was added at -65° C.
Stirring for 30 minutes was followed by addition of triethylamine (25.7 g, 254 mmol).
The cooling bath was removed 15 minutes after completed addition.
The reaction mixture was quenched with 1 M aqueous hydrochloric acid solution (152 ml, 152 mmol) at -10° C.
The layers were separated.
The organic layer was washed with two 250 ml-portions of water and one 100-ml portion of brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as yellow oil (9.3 g, quantitative), which was used in the next step without further purification. MS m/e: 170 (M⁺)

References:

HOFFMANN-LA ROCHE INC.;Dolente, Cosimo;Schnider, Patrick US2014/221350, 2014, A1 Location in patent:Paragraph 0168

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