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3 protocols using dichloromethane ch2cl2

1

Synthesis and Characterization of Ferulic Acid Esters

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Ferulic acid (99%) and triphenyl phosphine (99%) were purchased from Sigma-Aldrich Japan Co., Ltd. p-Coumaric acid (>98.0%), sinapinic acid (>98.0%), oxalyl chloride (>98.0%), and diisopropyl azodicarboxylate (40% in toluene, ca. 1.9 mol L−1) were purchased from Tokyo Chemical Industry Co., Ltd. Methyl ricinoleate (>97.0%), acetic anhydride (>97.0%), N,N-dimethylaminopyridine (DMAP) (>99.0%), N,N′-diisopropylcarbodiimide (DIC) (>99.0%), pyridine (>99.5%, dehydrated), N,N-dimethylformamide (DMF) (>99.5%, dehydrated), sodium sulphate (Na2SO4) (>99.0%), and tetrahydrofuran (THF) (>99.5%, with stabilizer, for gel permeation chromatography (GPC) grade) were purchased from FUJIFILM Wako Pure Chemical Corporation. p-Toluenesulfonic acid monohydrate (>99.0%) and lithium hydroxide monohydrate (>99.0%) were purchased from KISHIDA CHEMICAL Co., Ltd. Toluene (>99.5%, dehydrated), dichloromethane (CH2Cl2) (>99.5%, dehydrated), and THF (>99.5%, dehydrated stabilizer free) were purchased from Kanto Chemical and purified on a Glass Contour Solvent Purification System (NIKKO HANSEN & Co., Ltd, Japan). Chloroform-d1 (99.8 atom % D with 0.03 vol% tetramethylsilane) was purchased from Kanto Chemical. These chemicals were used without further purification unless otherwise noted. 4-(Dimethylamino)pyridinium p-toluenesulfonate (DPTS) was synthesised according to the literature.43 (link)
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2

Synthesis and Characterization of Polycaprolactone

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ε-Caprolactone (>99.0%) and 1,5,7-triazabicyclo[4.4.0]dec-5-ene
(TBD) (>98.0%) were purchased from Tokyo Chemical Industry Co.
Ltd.
(Tokyo, Japan). Ethanol (EtOH, >99.5%) and acetic acid (>99.7%)
were
purchased from Nacalai Tesque Inc. (Kyoto, Japan). Acetic anhydride
(>97%), ethyl acetate (EtOAc, >99.5%), n-hexane
(>96.0%),
chloroform (>99.0%), mEthanol (>99.8%), poly(ε-Caprolactone)
(PCL), DMSO for molecular biology, Evans blue, and sodium dodecyl
sulfate (SDS) for molecular biology were purchased from Fujifilm Wako
Pure Chemical Co. (Osaka, Japan). Dichloromethane (CH2Cl2, >99.5%) and tetrahydrofuran (THF, >99.5%) were purchased
from KANTO Chemical Co., Inc. (Tokyo, Japan) and were dried and deoxygenized
by passage through the columns of a Glass Contour Solvent System before
use. ε-Caprolactone was distilled from calcium hydride before
use. 6-Hydroxycaproic acid was synthesized as described in the literature.28 (link) EtOH was dried over 3 Å molecular sieves
before use. YCT was purchased from Recenttec K.K. (Tokyo, Japan). Chlorella sp. was purchased from Chlorella Industry Co.,
Ltd. (Tokyo, Japan). Marine Art SF-1 artificial seawater was purchased
from Osaka Yakken Co. Ltd. (Osaka, Japan).
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3

Synthesis and Characterization of Organometallic Complexes

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Unless noted otherwise, all synthetic operations and measurements were carried out under an atmosphere of N2 using Schlenk-line techniques. FeII(ClO4)2·6H2O, CuII(OAc)2·H2O (OAc=acetate), HCO2H, acetic acid (AcOH), ammonium acetate (NH4OAc), acetyl acetone, calcium oxide (CaO) and H2SO4 were purchased from Wako Pure Chemical Industries (Japan). Dehydrated MeOH, dichloromethane (CH2Cl2) and MeOH-d4 were purchased from Kanto Chemical Co. Inc. (Japan). TBAOH in MeOH (37%), which was used after the removal of MeOH, an aqueous solution of HCHO (37%), t-BuSH, t-Bu2S2, NADCl and apH2 were purchased from Tokyo Chemical Industry Co. Ltd. (Japan). Prior to use, apH2 was washed with CH2Cl2 and dried in vacuo for several minutes, while t-BuSH was used after stirring with CaO for 12 h, followed by distillation. MeOH-d3 was purchased from Sigma-Aldrich. APX was prepared according to a reported procedure63 . All solvents that were used under anaerobic conditions were thoroughly degassed by at least five freeze–pump–thaw cycles immediately prior to use. Although we did not experience any difficulties with perchlorate salts, these should be regarded as potentially explosive, and therefore handled with utmost care.
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