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[ CAS No. 1653-40-3 ] {[proInfo.proName]}

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Chemical Structure| 1653-40-3
Chemical Structure| 1653-40-3
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Product Details of [ 1653-40-3 ]

CAS No. :1653-40-3 MDL No. :MFCD00060842
Formula : C8H18O Boiling Point : -
Linear Structure Formula :- InChI Key :BWDBEAQIHAEVLV-UHFFFAOYSA-N
M.W : 130.23 Pubchem ID :15450
Synonyms :

Safety of [ 1653-40-3 ]

Signal Word:Warning Class:
Precautionary Statements:P210-P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P370+P378-P403+P233-P403+P235-P405-P501 UN#:
Hazard Statements:H315-H319-H335-H227 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1653-40-3 ]

* 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 [ 1653-40-3 ]

[ 1653-40-3 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 112-80-1 ]
  • [ 1653-40-3 ]
  • oleic acid-(6-methyl-heptyl ester) [ No CAS ]
YieldReaction ConditionsOperation in experiment
82.7% With Sulfated Zirconia type 1 at 140℃; for 4h; Autoclave; 2.2.1. Esterification of free fatty acid with alcohols General procedure: Esterification was carried out in a stainless steel autoclave reactor equipped with 30 ml of Teflon liner and a Teflon-coated magnetic stirring bar. A mixture of free fatty acid (6.25 mmol), alcohol (7.5 mmol), and catalyst (100 mg) was charged into the Teflon liner. The mixture was heated at 140 °C for 4 h with stirring at 300 rpm. After the reaction, the reaction mixture was cooled to room temperature, and the catalyst was separated from the reaction mixture by centrifuging. To test the recyclability of the catalyst, the catalyst was recovered after the reaction by washing three times with a mixture of hexane and acetone (hexane:acetone = 1:1). Then the catalyst was dried at 100 °C for 24 h. The reaction was repeated five times.
With toluene-4-sulfonic acid
With naphthalene-2-sulfonate
With lipase from Candida sp. 99-125 In neat (no solvent) at 20℃; for 24h; Molecular sieve; Enzymatic reaction; 2.2.1 General procedures of esterification General procedure: All the esterification experiments were carried out in a 50 mL round bottom flask. The reaction procedure was described as follows: To a mixture of 0.05 mol oleic acid and corresponding alcohol, catalyst was added at the given temperature. Normally, the reactants mixture kept stirring for 24 h until the reaction completed. The samples were taken out every 1 h in the first 12 h, and the acid value was determined according to the standard GB1668-81. In the end, the chromaticity of the oleates was recorded on PFX-i Series from Tintometer Ltd.

Reference： [1]Oh, Jinho; Yang, Sungeun; Kim, Chanyeon; Choi, Inchang; Kim, Jae Hyun; Lee, Hyunjoo [Applied Catalysis A: General, 2013, vol. 455, p. 164 - 171]
[2]Witnauer et al. [Industrial and Engineering Chemistry, 1955, vol. 47, p. 2304,2305] Teeter et al. [Journal of the American Chemical Society, 1951, vol. 73, p. 2302]
[3]Witnauer et al. [Industrial and Engineering Chemistry, 1955, vol. 47, p. 2304,2305] Teeter et al. [Journal of the American Chemical Society, 1951, vol. 73, p. 2302]
[4]Zhong, Hui; Fang, Zheng; Zou, Baohua; Li, Xin; Ouyang, Pingkai; Guo, Kai [Journal of Molecular Catalysis B: Enzymatic, 2013, vol. 90, p. 114 - 117]
  • 2
  • [ 929-10-2 ]
  • [ 1653-40-3 ]
YieldReaction ConditionsOperation in experiment
92% With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;
With lithium aluminium tetrahydride
Reference： [1]Tate, Daniel J.; Anemian, Remi; Bushby, Richard J.; Nanan, Suwat; Warriner, Stuart L.; Whitaker, Benjamin J. [Beilstein Journal of Organic Chemistry, 2012, vol. 8, p. 120 - 128]
[2]Milburn; Truter [Journal of the Chemical Society, 1954, p. 3344,3347]
  • 3
  • [ 85-44-9 ]
  • [ 1653-40-3 ]
  • [ 131-20-4 ]
YieldReaction ConditionsOperation in experiment
92% With pyrographite; toluene-4-sulfonic acid for 0.0152778h; Microwave irradiation (525 W);
With phospho-tungstic acid; phosphotungstic acid
Reference： [1]Fan, Xingjun; Yuan, Keguo; Hao, Caili; Li, Nan; Tan, Ganzu; Yu, Xianda [Organic Preparations and Procedures International, 2000, vol. 32, # 3, p. 287 - 290]
[2]Kim, Yoo Joong; Jonas, Jiri [Journal of Physical Chemistry A, 1998, vol. 102, # 17, p. 2778 - 2784]
  • 4
  • [ 75-21-8 ]
  • [ 626-88-0 ]
  • [ 1653-40-3 ]
Reference： [1]Journal of Chemical Ecology,1995,vol. 21,p. 1745 - 1762
  • 5
  • [ 1653-40-3 ]
  • [ 929-10-2 ]
YieldReaction ConditionsOperation in experiment
80% With potassium hydroxide In acetonitrile at 70℃;
With chromium(VI) oxide; sulfuric acid In water; acetone at 0 - 20℃; for 8h;
86 %Chromat. With water; potassium carbonate at 80℃;
Multi-step reaction with 2 steps 1.1: zinc(II) oxide; sodium hydroxide / 240 °C / 22502.3 Torr / Inert atmosphere; Autoclave; Large scale 1.2: 0.5 h / 150 °C / 760.05 Torr / Large scale 2.1: chloroacetic acid / water / 0.5 h / 40 °C / Large scale

Reference： [1]Hosseinzadeh, Shahram Zare; Babazadeh, Mirzaagha; Shahverdizadeh, Gholam Hossein; Hosseinzadeh-Khanmiri, Rahim [New Journal of Chemistry, 2019, vol. 43, # 24, p. 9491 - 9499]
[2]Chavan, Subhash P.; Pasupathy; Shivasankar [Synthetic Communications, 2004, vol. 34, # 3, p. 397 - 404]
[3]Vessally, Esmail; Ghasemisarabbadeih, Mostafa; Ekhteyari, Zeynab; Hosseinzadeh-Khanmiri, Rahim; Ghorbani-Kalhor, Ebrahim; Ejlali, Ladan [RSC Advances, 2016, vol. 6, # 108, p. 106769 - 106777]
[4]Current Patent Assignee: TAIAN HAVAY CHEMICALS - CN106278875, 2017, A
  • 6
  • [ 1653-40-3 ]
  • [ 117692-89-4 ]
  • [ 929-10-2 ]
YieldReaction ConditionsOperation in experiment
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; titanium(IV) oxide In benzotrifluoride for 12h; Irradiation;
Reference： [1]Zhang, Miao; Wang, Qi; Chen, Chuncheng; Ma, Wanhong; Zhao, Jincai; Zang, Ling [Angewandte Chemie - International Edition, 2009, vol. 48, # 33, p. 6081 - 6084][Angewandte Chemie, 2009, vol. 121, # 33, p. 6197 - 6200]
  • 7
  • [ 1653-40-3 ]
  • [ 636-46-4 ]
  • 4-hydroxy-1,3-benzenedicarboxylic acid diisooctyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
89.5% With sodium hydrogen sulfate; In N,N-dimethyl-formamide; at 150℃; (0.01 mol) of <strong>[636-46-4]4-hydroxy-1,3-benzenedicarboxylic acid</strong>, 0.26 g of NaHSO4, 30 ml of isooctanol and 5 ml of DMF were added, and the reaction was stirred at 150 C. TLC was followed until the starting point disappeared.The reaction mixture was extracted with ethyl acetate, washed with saturated sodium hydrogencarbonate solution and saturated brine successively, dried over anhydrous sodium sulfate, and ethyl acetate was distilled off under reduced pressure. The residual liquid was distilled under reduced pressure to distill off excess isooctanol 92 C / 170 Pa) to give 3.66 g of the title compound as a pale yellow liquid.Yield: 89.5%
Reference： [1]Patent: CN105884620,2016,A .Location in patent: Paragraph 0041; 0042
  • 8
  • [ 1653-40-3 ]
  • [ 100-21-0 ]
  • [ 6422-86-2 ]
YieldReaction ConditionsOperation in experiment
With titanium(IV) isopropylate; monobutyltin triisooctanoate at 150 - 230℃; for 2h; 2 Ingredients: terephthalic acid, iso-octanol, tetrabutyl titanate, monobutyltin triisooctanoate tin; Submit CorrectionsCloseThe amount of alcohol to acid ratio 2.81 of isooctyl alcohol and terephthalic acid into the reactor and heated to 150 ° C dehydration, then add accounting terephthalic 0.15% wt of tetrabutyl titanate and 0.1% wt monobutyl tin triisooctanoate heating and stirring continuously out of the system during the reaction generated water, iso-octanol reflux. 2.81150°C0.15%wt0.1%wt Submit CorrectionsCloseRaising the temperature to 230 ° C, the reaction took 2 hours, when the reaction to the acid value
Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF FORESTRY - CN103896777, 2016, B Location in patent: Paragraph 0017-0019
  • 9
  • [ 1653-40-3 ]
  • [ 95-47-6 ]
  • [ 131-20-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: o-xylene With oxygen; 1-butylpyridinium bromide at 200℃; for 1h; Stage #2: 6-methylheptanol With trifluoroacetic acid at 150℃; for 0.5h; 8 Example 8 General procedure: In the continuous reaction apparatus, a mixture of o-xylene, dimethyl phthalate, manganese acetate, cobalt acetate and potassium acetate was poured into an oxidation reaction tube (the reaction mixture had a cobalt, manganese and potassium ion concentration of 300 ppm each, O-xylene concentration of 30%), filled with 3MPa oxygen, 200 ° C under the oxidation, reaction residence time of 2h. The mixture of the oxidized mixture and the methanol was poured into an esterification reaction tube (molecular weight ratio of methanol to starting o-xylene) of 10: 1, The mass ratio of molecular weight of aluminum silicate phosphate to starting o-xylene was 1: 100), and the reaction time was 3h at 150 ° c. After the esterification reaction, the mixture is oxidized to the second methyl group on the benzene ring, and then the esterification reaction is carried out in the esterification reaction tube. After the reaction, the mixture was subjected to gas chromatography and liquid chromatography to calculate the one-way conversion of o-xylene and the selectivity of dimethyl phthalate. The specific practice of Examples 2 to 18 is similar to that of Example 1, and the specific reaction conditions and results are shown in Table 1.
Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES; Dalian Institute of Chemical Physics (in: CAS) - CN104418748, 2016, B Location in patent: Paragraph 0020-0023; 0026
  • 10
  • [ 1653-40-3 ]
  • [ 1076-97-7 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
98.6% With HY zeolite molecular sieve at 160℃; for 2.5h; 8 The reaction was carried out in a 500 mL four-necked flask equipped with a stirrer, a water separator and a thermometer. Followed by adding 100.0 g1,4-cyclohexanedicarboxylic acid,160.0 g isooctanol and2.0g HY molecular sieve. The reaction temperature was controlled at 160 ° C until the reaction was stopped and the reaction was stopped for a total of 2.5 h. Cooled to 80 ° C, filter recovery catalyst. Reaction conversion rate 99.8%, selectivity 98.8%, single pass yield 98.6%.
Reference： [1]Current Patent Assignee: JIANGSU QINGQUAN CHEMICAL - CN105732370, 2016, A Location in patent: Paragraph 0032; 0033
  • 11
  • [ 1653-40-3 ]
  • [ 6386-38-5 ]
  • 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid isooctyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
98.28% With lithium carbonate; at 140 - 180℃; for 4h;Inert atmosphere; In a 500 ml four-necked flask equipped with an electric stir, a thermometer, a vacuum tube, a condenser and a cold trap,73 g (0.25 mol)3,5-di-tert-butyl-4-hydroxyphenylpropionate (3,5-methyl ester)42.5 g (0.325 mol) of isooctanol, 0.07 g of lithium carbonate,Vacuum nitrogen replacement more than 3 times, heating to 140 ~ 150 ,Adjust the vacuum to -0.04 ~ -0.05MPa, the reaction process of methanol continue to extract, collected in the cold trap,In this condition to maintain the reaction 1h, continue to heat up to 160 ~ 170 , adjust the vacuum to keep it in the -0.07 ~ -0.08MPa, by-product of methanol continue to slip out, collected in the cold trap,And isooctanol was refluxed into the reaction system, and the reaction was maintained for 3 hours under this condition, and the temperature was raised to 180 C,Start to adjust the vacuum to -0.096MPa below the steam off the excess isooctanol, remove the end of 2h.Cooling to 90 C, nitrogen to atmospheric pressure, adding 0.35 g of citric acid to the reaction system, neutralizing the reaction for 1 h,Hot filtered to give 86 g of colorless transparent liquid product, product yield: 98.28%.
Reference： [1]Patent: CN104447333,2016,B .Location in patent: Paragraph 0025-0026
  • 12
  • [ 1653-40-3 ]
  • [ 79-20-9 ]
  • [ 103-09-3 ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid at 65℃; for 4h; 4 Example 4 In the mechanical stirrer, reflux condenser and a thermometer of the 1000 ml flask of three sequentially added in the methyl acetate 296 g, isooctanol 260 g toluene sulfonic acid and 13.0 g, stir, for 65 °C reaction 4 hours. By reducing pressure low boiling, then adding to the methoxy benzaldehyde 180 g, dropping 30% of 36 g liquid sodium methoxide. The reaction temperature is raised to 90 °C, reaction 4 hours later. Gradually adding glacial acetic acid 7.9 g out-in and. By reducing pressure low boiling, filtering to remove the mother liquor solids, then the gas phase chromatography analysis, calculated in the mother liquor to the methoxy cinnamic acid ester product 376 g, yield 98.2%.
Reference： [1]Current Patent Assignee: QINGDAO UNIVERSITY OF SCIENCE AND TECHNOLOGY; SHANDONG DAGUAN BIOCHEMICAL TECH - CN107522616, 2017, A Location in patent: Paragraph 0024-0033
  • 13
  • [ 1653-40-3 ]
  • [ 1928-38-7 ]
  • [ 3035-67-4 ]
YieldReaction ConditionsOperation in experiment
98.44% at 100℃; for 2h; Large scale; 1; 8; 10; 11; 1; 2 To the methyl 2,4-dichlorophenoxyacetate, 132.71 g of 99% isooctanol and 1.41 g of Na/NaOH/γ-Al 2 O 3 were added and reacted at 100 ° C for 2 h.At the same time, the alcohol formed by the reaction was distilled off, and the reaction was filtered to obtain 332.74 g of isooctyl 2,4-dichlorophenoxyacetate, the content was 98.6%, and the total yield was 98.44% based on phenol.
332.88 g With macroporous styrene strong acid cation exchange resin D001H at 130℃; for 4h; 1.3 To the obtained methyl 2,4-dichlorophenoxyacetate,Add 137.77 g of 99% pure isooctanol and 1.87 gMacroporous styrene strong acid cation exchange resin D001H,The reaction was carried out at 130 ° C for 4 h while distilling off the alcohol formed by the reaction.After the reaction was filtered, 332.88 g of 2,4-dichlorophenoxyacetic acid isooctyl ester was obtained.
333.23 g With macroporous styrene strong acid cation exchange resin D001H at 130℃; 1; 1; 2 To the methyl 2,4-dichlorophenoxyacetate obtained by distillation, 138.47 g of 99% isooctanol and 1.89 g were added.Macroporous styrene strong acid cationExchange resin D001H as a catalyst,The reaction is carried out at 130 ° C and the resulting alcohol is distilled off.Filtered after reaction333.23g of 2,4-dichlorophenoxyacetic acid isooctyl ester,98.6%,The yield was 98.59% based on methyl phenoxyacetate.
Reference： [1]Current Patent Assignee: SHANDONG RAINBOW INVESTMENT CO., LTD. - CN108947837, 2018, A Location in patent: Paragraph 0070; 0073; 0100; 0103; 0108; 0111; 0112
[2]Current Patent Assignee: SHANDONG RAINBOW INVESTMENT CO., LTD. - CN108947814, 2018, A Location in patent: Paragraph 0066; 0069; 0073; 0077; 0081
[3]Current Patent Assignee: SHANDONG RAINBOW INVESTMENT CO., LTD. - CN108947815, 2018, A Location in patent: Paragraph 0060; 0062; 0064; 0066; 0067; 0069
  • 14
  • [ 1653-40-3 ]
  • [ 4841-22-9 ]
  • isooctyl 4-chlorophenoxyacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
299.03 g With aluminum oxide; sodium; sodium hydroxide; In diethylene glycol; at 100℃; for 2h; To the obtained <strong>[4841-22-9]methyl 4-chlorophenoxyacetate</strong>, 134.11 g of 99% pure isooctanol and 1.21 g of Na/NaOH/gamma-Al 2 O 3 (according to Gorzawski H., Hoelderich W. F.. Transesterification of methyl benzoate) were added.And dimethyl terephthalate with ethylene glycol over superbases [J]. Applied catalysis, 1999, 179: 131-137 prepared by the method), reacted at 100 C for 2 h, while distilling off the alcohol formed by the reaction,After completion of the reaction, filtration was carried out to obtain 299.03 g of isooctyl 4-chlorophenoxyacetate, the content was 98.6%, and the total yield was 98.66% based on phenol.
Reference： [1]Patent: CN108947814,2018,A .Location in patent: Paragraph 0106; 0109
  • 15
  • [ 1653-40-3 ]
  • [ 94-80-4 ]
  • [ 3035-67-4 ]
YieldReaction ConditionsOperation in experiment
330.87 g With macroporous styrene strong basic anion exchange resin D201OH at 120℃; for 4h; 9.3; 11.3 To the obtained n-butyl 2,4-dichlorophenoxyacetate,Add 139.94g of 99% pure isooctanol and1.87g macroporous styrene strong basic anion exchange resin D201OH,The reaction was carried out at 120 ° C for 4 h while distilling off the alcohol formed by the reaction.After the reaction was filtered, 330.87 g of isooctyl 2,4-dichlorophenoxyacetate was obtained.The content was 98.8%, and the total yield was 98.18% based on phenol.
Reference： [1]Current Patent Assignee: SHANDONG RAINBOW INVESTMENT CO., LTD. - CN108947814, 2018, A Location in patent: Paragraph 0110; 0113; 0118; 0121
  • 16
  • [ 1653-40-3 ]
  • [ 85-42-7 ]
  • [ 1028279-92-6 ]
YieldReaction ConditionsOperation in experiment
98.8% With C9H21NO3S*H2O4S; at 160 - 180℃; for 2.5h; Add hexahydrophthalic anhydride (51.3g), isooctyl alcohol (121.3g) and 0.86g of catalyst A to a 500ml three-necked flask,The reaction was stirred and heated under normal pressure, and the temperature was maintained at 160-180 C for 2.5 hours.The esterified layer was separated from the reaction solution, and the obtained product was stripped of unreacted alcohol at 0.009 MPa and a temperature of 160 C.After cooling to room temperature, the final product, diisooctyl cyclohexane 1,2-dicarboxylate, is obtained after decolorization, alkaline washing, water washing, pressure filtration, and steam stripping.The product is a colorless transparent oily liquid. The yield was 98.8% and the purity was 99.4%.
Reference： [1]Patent: CN110713439,2020,A .Location in patent: Paragraph 0018-0024
  • 17
  • [ 1653-40-3 ]
  • [ 5026-76-6 ]
  • [ 929-10-2 ]
YieldReaction ConditionsOperation in experiment
1: 39% 2: 59% With cobalt(II) trifluoromethanesulfonate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In acetone at 100℃; for 30h; 4 Example 4 In a 250ml pressure-resistant reactor with quartz lining (equipped with a back pressure valve), add isooctyl alcohol (14.98g, 115mmol), cobalt(II) triflate (0.19g, 1.0mmol), TEMPO (0.12g) , 0.8mmol), 102ml of acetone, and then use oxygen to replace the air in the reactor, and continue to ventilate to control the pressure in the kettle to 1.1Mp, maintain the pressure and continue to inject oxygen, reflux and stir at 100°C for 30 hours. After the reaction, the reaction liquid was cooled to room temperature, filtered to remove the solid material, the liquid was separated by distillation to obtain the product isooctanoic acid and the product isooctene, the conversion of isooctanoic acid was 88%, the yield of isooctanoic acid was 59%, The olefin yield was 39%.
Reference： [1]Current Patent Assignee: Dalian Institute of Chemical Physics (in: CAS); CHINESE ACADEMY OF SCIENCES - CN112079707, 2020, A Location in patent: Paragraph 0036-0037

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