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Chemical Structure| 3144-54-5 Chemical Structure| 3144-54-5

Structure of 3144-54-5

Chemical Structure| 3144-54-5

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Product Details of [ 3144-54-5 ]

CAS No. :3144-54-5
Formula : C12H16O3
M.W : 208.25
SMILES Code : CCCCCC(C1=CC=C(O)C=C1O)=O
MDL No. :MFCD00002281

Safety of [ 3144-54-5 ]

Application In Synthesis of [ 3144-54-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 3144-54-5 ]

[ 3144-54-5 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 3144-54-5 ]
  • [ 136-77-6 ]
YieldReaction ConditionsOperation in experiment
86.2% With palladium 10% on activated carbon; hydrogen; In methanol; at 80℃; under 11251.1 Torr;Autoclave; In a 1.0 L autoclave, 104.1 g (0.5 mol) of 4-hexanoylresorcinol was added.Add 500ml of methanol,10% wet Pd/C (20.0 g),Heated to 80 C,Hydrogen gas was introduced at a pressure of 1.5 MPa and the GC was followed until the end of the reaction.The reaction solution was filtered to recover Pd/C, and the filtrate was concentrated to a light brown-red oily liquid.Recrystallization from dichloromethane and n-hexane gave 83.7 g of 4-hexyl resorcinol,GC>99.0%, yield 86.2%, total yield 77.5% over two steps.
With hydrogen;nickel; In methanol; at 70 - 95℃; under 7500.75 - 37503.8 Torr;Product distribution / selectivity; 85 g 4-caproylresorcinol is dissolved in 770 mL of MeOH. 25 g Ni-catalyst are added and the mixture is hydrogenated at 70 C. and 10 bar. The GC quality of the crude material is 94%. The catalyst is filtered off, most of the MeOH is distilled off, 350 mL of toluene are added and the mixture is distilled until the head temperature indicates full removal of the MeOH. The mixture is cooled to room temperature, and the product is filtered off and dried.; 85 g 4-caproylresorcinol (derived from the Example 5, HF-process) is dissolved in 255 mL of MeOH. 10 g Ni-catalyst are added and the mixture is hydrogenated at 80-95 C. and 30-50 bar. The GC quality of the crude material is only 86%. The catalyst is filtered off, most of the MeOH is distilled off, 350 mL of toluene are added and the mixture is distilled until the head temperature indicates full removal of the MeOH. The mixture is cooled to room temperature, and the product is filtered off and dried.
With hydrogenchloride; zinc; In ethanol; water;Heating / reflux; Given the known sensitivity issues associated with commercial grade hexylresorcinol, evaluation of the skin sensitivity to the purified hexylresorcinol was also evaluated. Skin sensitivity was evaluated following the method cited in the reference Appraisal of the Safety of Chemicals in Food, Drugs and Cosmetics, published by The <n="21"/>Association of Food and Drug Officials of The United States. The specific method employed used nine inductive patchings, not the ten cited in the reference, under occlusive patch conditions.[0059] Highly pure hexylresorcinol was prepared as follows: A mixture comprising 40 grams hexanoic acid, 6.0 grams zinc chloride and 30 ml of xylene was heated to reflux. 10 grams of resorcinol was gradually added to the foregoing and mixture allowed to reflux for 4 to 6 hours. Water formed during the reaction was removed by the addition of xylene through azeotropic distillation. Thereafter, the reaction mixture was poured into 100 ml of water and the organic layer separated. The separated organic layer was then subjected to fractional distillation to recover the solvent, hexanoic acid and the 4-hexanoylresorcinol. The distilled product was then crystallized from hexane to yield approximately 15 grams crude hexanoylresorcinol. 15 grams hexanoylresorcinol was then dissolved in 30 ml of ethanol and treated with 18 grams of activated zinc and 60 ml of 25% hydrochloric acid at mild reflux. After completion of the reaction the ethanol is removed and the reaction mixture is extracted with toluene. The organic layer is washed with water (30 ml - 2 times) and concentrated to dryness to give a crude hexylresorcinol (yield 13gm). This on crystallization from hexane gave 10 grams of hexylresorcinol having resorcinol content of 0.005% to nil.[0060] Samples were prepared for evaluation by diluting the highly pure hexylresorcinol in corn oil to a 5% concentration, with dilutions freshly prepared on each application day. 0.2 ml of the diluted test material was dispensed onto occlusive, hypoallergenic patches and the treated patches applied directly to the skin of the infrascapular regions of the back, to the right or left of the midline of each subject: one hundred and eleven subjects were employed. After application of the patch, each subject was dismissed with instructions not to wet or expose the test area to direct sunlight. The patch was removed by the subject after 24 hours. This procedure was repeated every Monday, Wednesday and Friday for three consecutive weeks until a series of nine consecutive 24 hour exposures had been made. During the test period, the test area on the subjects' backs were observed for evidence of edema or erythema just before applications two through nine and the next test date following application nine. If evidence of a reaction was found, the area of edema and/or erythema was then measured and recorded: edema being estimated by an evaluation of the skin with respect to the contour of the <n="22"/>unaffected normal skin. The subjects were then given a 10 - 14 day rest period after which a challenge or retest patch saturated with 0.2 ml of the hexylresorcinol dilutions was applied to a previously unexposed test site. The challenge or retest sites were monitored and scored 24 and 48 hours after application. Based on the test results, the 5% dilution in corn oil of the purified hexylresorcinol was determined to be a NON-PRIMARY IRRITANT and a NON-PRIMARY SENSITIZER according to the reference.
 

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