The Hydrolysis of Some β-Alkoxypropionitriles<sup>1</sup>

Christian, Robert; Hixon, R. M.

doi:10.1021/ja01184a014

Cited by 27 publications

(4 citation statements)

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“…The ß-alkoxypropionic acids were converted to their p-bromophenacyl esters. M.ps., ßmethoxy, 69-70°; ß-propoxy, 59-60°; 0-isobutoxy, 60-61°; these values are in reasonable agreement with the literature (8). was immersed in an ice-bath and sodium hydroxide pellets were added to the butynediol in 20-g. portions.…”

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confidence: 87%

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Some Reactions of 2-Butyne-1,4-Diol

Hennion¹,

Kupiecki²

1953

J. Org. Chem.

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confidence: 87%

“…Special interest attached to the ethoxy compound, in view of Henshall's claim (6). Oxidation gave the known ß-ethoxypropionic acid (III, R = C2H6), whose p-bromphenacyl ester (IV) had the correct m.p., not depressed by admixture with an authentic sample (8). The IR spectrum of II (R = C2H6) showed the typical hydroxyl band at 2.9µ and the carbonyl at 5.8µ.…”

mentioning

confidence: 95%

Some Reactions of 2-Butyne-1,4-Diol

Hennion¹,

Kupiecki²

1953

J. Org. Chem.

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“…The colorless oil had a bp of 130-133°/2.7 torr. AMenthoxybutanoic acid (IV) could not be prepared by general methods of either alkaline (2) or acid (4) hydrolysis for alkoxynitriles. Instead, it was prepared by the reactions of sodium Amenthoxide and 4-chlorobutanoic acid according to the method used for the synthesis of Amenthoxyacetic acid (5).…”

Section: Literature Citedmentioning

confidence: 99%

Synthesis of certain l-menthol compounds

Gibbs¹,

Krottinger²,

Palma³

1976

J. Chem. Eng. Data

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nuclidine are approximately additive and lead to an average reduction in pKa of 2.8 pK units per benzo substitution. This relationship is shown in Figure 2.Experimental Anhydrous HOAc was prepared by distillation from triacetyl borate following Eichelberger. and LaMer (5). Analysis of the distillate by the method of Bruckenstein ( 7) revealed no detectable H20. The -0. l N HCI04 titrant in anhydrous HOAc was prepared by adding 5.1 mi acetic anhydride to 2.2 ml of 70% HC104 in 70 ml HOAc. The mixture was then diluted to 250 ml with HOAc and allowed to stand for several days before use. The NaOAc was dried at 110'C for 24 hr prior to the preparation of the standard solution.The titrations were carried out in a constant temperature bath at 25' f 0.5'C using a Leeds and Northrup Model 7403-A2 pH meter. A Leeds and Northrup #1199-72 glass electrode was used as the indicating electrode, and the reference electrode was a modified calomel electrode containing a saturated solution of NaCI, NaC104, and Hg2C12 in anhydrous HOAc (4). Samples containing -0.06 meq base in 20 ml HOAc were titrated with the HCIO4 titrant using a 10-ml microburet. Prepurified N2, dried by passing through a Drierite drying tower and saturated with HOAc by bubbling through anhydrous HOAc, was passed over the solutions throughout the titrations.The preliminary experiment was run in anhydrous HOAc with a Sargent S-300072-15 combination electrode. The 0and mchloroaniline, used as references, were purified by distillation. Literature Cited(1) Bruckenstein.

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“…Halogen analyses eliminated the possibility of a 3-alkoxy-substituted component. Hydrolysis of an imidate hydrochloride normally forms the corresponding ester and ammonium chloride1 23 4567(eq 6) but hydrolysis of 1 gave 5 and NH4Br in RC(OR')=NH2+Cl-+ H20 -> RCOOR' + NH4C1 (6) addition to 4 and NH4C1. Pyrolysis of an imidate hydrochloride usually proceeds smoothly to the corresponding amide and alkyl chloride3 (eq 7) but pyrolysis heat RC(OR')=NH2+Cl-->-RCONHj + R'Cl (7) of 1 gave alkyl bromide and 3-chloropropionamide.…”

mentioning

confidence: 99%