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[ CAS No. 843666-27-3 ]

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2D
Chemical Structure| 843666-27-3
Chemical Structure| 843666-27-3
Structure of 843666-27-3 *Storage: {[proInfo.prStorage]}

Quality Control of [ 843666-27-3 ]

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Related Doc. of [ 843666-27-3 ]

SDS

Product Details of [ 843666-27-3 ]

CAS No. :843666-27-3MDL No. :MFCD23136039
Formula :C20H38O4Boiling Point :-
Linear Structure Formula :-InChI Key :N/A
M.W :342.51Pubchem ID :57817723
Synonyms :

Computed Properties of [ 843666-27-3 ]

TPSA : 63.6 H-Bond Acceptor Count : 4
XLogP3 : 6.7 H-Bond Donor Count : 1
SP3 : 0.90 Rotatable Bond Count : 17

Safety of [ 843666-27-3 ]

Signal Word:WarningClassN/A
Precautionary Statements:P280UN#:N/A
Hazard Statements:H302-H312-H332Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 843666-27-3 ]

  • Upstream synthesis route of [ 843666-27-3 ]
  • Downstream synthetic route of [ 843666-27-3 ]

[ 843666-27-3 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 505-54-4 ]
  • [ 36805-97-7 ]
  • [ 843666-27-3 ]
YieldReaction ConditionsOperation in experiment
47.6% Reflux Hexadecanedioic acid (4.5 g, 15.71 mmol) was suspended in Toluene (28.1 ml) and the mixture was heated to reflux. 1,1 -di-tert-butoxy-N,Ndimethylmethanamine (10.10 ml, 42.1 mmol) was added drop-wise over 30 mm. Themixture was reflux overnight. The solvent was removed in vacuo at 50°C and the crude material was suspended in CH2C12/EtOAc (75 mL. 1:1) ans stirred for 15 mm. The solids were removed by filtration and washed with CH2C12 (25 mL). The filtration was evaporated in vacuo. The resulting material was suspended in CH2C12 (6 mL), cooled with ice for 10 mins, and filtered. The solvent was removed invacuo to leave crude product which was purified by flash chromatography (silic gel,EtOAc/Hexane) to get 16-(tert-butoxy)-16-oxohexadecanoic acid (2.56 g, 7.47 mmol,47.6 percent yield). Analysis condition D: Retention time = 5.04 mm; ESI-MS(+) m/z269.3 [M — OC(CH3)3]; ‘H NMR (500MHz, METHANOL-d4) ö 2.33 - 2.18 (m, 4H),1.66 - 1.54 (m, 4H), 1.50 - 1.43 (m, 9H), 1.40 - 1.25 (m, 20H).
33%
Stage #1: at 50℃;
Stage #2: With ethyl acetate In dichloromethane for 0.25 h;
Hexadecadioic acid (40.0 g, 140 mmol) was suspended in toluene (250 ml) and the mixture was heated to reflux. λ/,λ/-dimethylformamide di-tert-butyl acetal (76.3 g, 375 mmol) was added drop-wise over 4 hours. The mixture was refluxed overnight. The solvent was removed in vacuo at 50 0C, and the crude material was suspended in DCM/AcOEt (500 ml, 1 :1 ) and stirred for 15 mins. The solids were collected by filtration and triturated with DCM (200 ml). The filtrated were evaporated in vacuo to give crude mono-tert-butyl hexadecandioate, 30 grams. This material was suspended in DCM (50 ml), cooled with ice for 10 mins, and filtered. The solvent was removed in vacuo to leave 25 gram crude mono- tert-butyl hexadecandioate, which was recrystallized from heptane (200 ml) to give mono- tert-butyl hexadecandioate, 15.9 g (33 percent).1H-NMR (CDCI3) δ: 2.35 (t, 2H), 2.20 (t, 2H), 1.65-1.55 (m, 4H), 1.44 (s, 9H), 1.34- 1.20 (m, 20 H).
33% Reflux Hexadecandioic acid (40.0 g, 140 mmol) was suspended in toluene (250 ml) and the mixture was heated toreflux. N,N-Dimethylformamide di-tert-butyl acetal (76.3 g, 375 mmol) was added drop-wise over 4 hours. The mixturewas refluxed overnight. The solvent was removed in vacuo at 50 °C, and the crude material was suspended in dichloromethane/ethyl acetate (500 ml, 1:1) and stirred for 15 mins. The solids were collected by filtration and triturated withdichloromethane (200 ml). The filtrated were evaporated in vacuo to give crude mono-tert-butyl hexadecandioate, 30grams. This material was suspended in dichloromethane (50 ml), cooled with ice for 10 mins, and filtered. The solventwas removed in vacuo to leave 25 gram crude mono-tert-butyl hexadecandioate, which was recrystallized from heptane(200 ml) to give mono-tert-butyl hexadecandioate, 15.9 g (33 percent). Alternatively to recrystallization, the mono-ester canbe purified by silica chromatography with ethyl acetate/heptane. 1H-NMR (CDCl3) δ: 2.35 (t, 2H), 2.20 (t, 2H), 1.65-1.55(m, 4H), 1.44 (s, 9H), 1.34-1.20 (m, 20 H).
33% for 4.00 h; Reflux The hexadecanedioic acid (20.0 g, 69.8 mmol) was suspended in toluene (125 ml) according to the process for the preparation of tert-butyl hexadecanedioate disclosed in No. 4 of Novo Nordisk Company Patent No. CN1829738.The mixture was heated to reflux. N,N-dimethylformamide di-tert-butyl acetal (38.2 g, 187.5 mmol) was added dropwise over 4 hours and the mixture was refluxed overnight. Remove the solvent in vacuo at 50°C,It was suspended in DCM/AcOEt (250 ml, 1:1) and stirred for 15 minutes. The solid was collected by filtration, resuspended by the addition of DCM (50 ml), and the filtrate was collected by filtration, distilled under reduced pressure, and the resulting product was suspended in DCM (25 ml) pre-cooled to 0°C.The temperature was reduced to 4°C, and the solvent was distilled off under reduced pressure. Recrystallization from n-heptane (100 ml) gave 7.9 g (33percent) of mono-tert-butyl hexadecanedioate, which was not suitable for industrial scale-up.

Reference: [1] Patent: WO2016/77518, 2016, A1. Location in patent: Page/Page column 477; 478
[2] Patent: WO2007/128817, 2007, A2. Location in patent: Page/Page column 81
[3] Patent: EP2448962, 2016, B1. Location in patent: Paragraph 0051
[4] Patent: CN105001140, 2018, B. Location in patent: Paragraph 0177-0179
[5] Patent: US2010/22446, 2010, A1
  • 2
  • [ 505-54-4 ]
  • [ 75-65-0 ]
  • [ 843666-27-3 ]
Reference: [1] Patent: US2015/183847, 2015, A1. Location in patent: Page/Page column
  • 3
  • [ 505-54-4 ]
  • [ 843666-27-3 ]
Reference: [1] Patent: CN105001140, 2018, B
  • 4
  • [ 34959-19-8 ]
  • [ 843666-27-3 ]
Reference: [1] Patent: CN105001140, 2018, B
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