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515-84-4

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515-84-4 Usage

Chemical Properties

Colorless liquid with a menthol-like odor. It is miscible with ethanol, ether and benzene, but insoluble in water.

Uses

Ethyl trichloroacetate was used in the synthesis of dichlorocarbon precursor, phenyl(trichloromethyl)methyl.

Preparation

Ethyl trichloroacetate is synthesized from trichloroacetic acid and ethyl alcohol by the esterification reaction. synthesis steps: Trichloroacetic acid(TCA), anhydrous ethyl alcohol and sulfuric acid are heated together and refluxed for 6 h. After cooling, the ester layer is separated by pouring into water, neutralized with 5-10% sodium carbonate solution, washed with water and dried overnight with anhydrous calcium chloride. After filtration, distillation was carried out to obtain the finished product. Yield 75%.

Application

Ethyl trichloroacetate can be used as solvent, organic synthesis, perfume and pharmaceutical intermediates.

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 3519, 1981 DOI: 10.1021/jo00330a028

General Description

Ethyl trichloroacetate undergoes atom-transfer radical addition reaction with styrene catalyzed by the Ru-pentamethylcyclopentadienyl complexes.

Purification Methods

Shake the ester with saturated aqueous Na2CO3 (three times), aqueous 50% CaCl2 (three times), saturated aqueous NaCl (twice), then distil over CaCl2 and redistil it under reduced pressure. [Beilstein 2 IV 514.]

Check Digit Verification of cas no

The CAS Registry Mumber 515-84-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,1 and 5 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 515-84:
(5*5)+(4*1)+(3*5)+(2*8)+(1*4)=64
64 % 10 = 4
So 515-84-4 is a valid CAS Registry Number.
InChI:InChI=1/C4H5Cl3O2/c1-2-9-3(8)4(5,6)7/h2H2,1H3

515-84-4Synthetic route

ethanol
64-17-5

ethanol

trichloroacetic acid
76-03-9

trichloroacetic acid

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

Conditions
ConditionsYield
With sulfuric acid for 7h; Reflux;85%
With sodium hydrogen sulfate for 2h; Esterification; Heating;84.5%
With phosphorus pentoxide; copper(II) sulfate; sodium sulfate for 2h; Heating;41%
diethyl (trichloromethyl)phosphonate
866-23-9

diethyl (trichloromethyl)phosphonate

trichloroacetic acid
76-03-9

trichloroacetic acid

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

Conditions
ConditionsYield
at 120℃; for 24h;77%
acetaldehyde
75-07-0

acetaldehyde

1-ethoxyethyl trichloroethanoate

1-ethoxyethyl trichloroethanoate

triethyl phosphite
122-52-1

triethyl phosphite

A

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

B

diethyl 1-(1-ethoxyethyl)ethylphosphonate
69054-05-3

diethyl 1-(1-ethoxyethyl)ethylphosphonate

Conditions
ConditionsYield
A n/a
B 76%
1,1,2,2-tetrachloroethylene
127-18-4

1,1,2,2-tetrachloroethylene

ethanol
64-17-5

ethanol

ethyl acetate
141-78-6

ethyl acetate

A

freon-111
354-56-3

freon-111

B

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

Conditions
ConditionsYield
With chlorine monofluoride 1.) Freon 113; 2.) 20 - 25 deg C, 30 min.; Yield given. Multistep reaction;A 68%
B n/a
1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

ethanol
64-17-5

ethanol

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

Conditions
ConditionsYield
With N,N-dimethyl-formamide at 55℃; for 9h; Product distribution; other times, other temperatures;98 % Chromat.
With aluminum ethoxide
With N,N-dimethyl-formamide at 55℃; for 9h;98 % Chromat.
trichloro-acetic acid-(1-ethoxy-4,4,4-trichloro-3-oxo-but-1-enyl ester)
100191-69-3

trichloro-acetic acid-(1-ethoxy-4,4,4-trichloro-3-oxo-but-1-enyl ester)

ethanol
64-17-5

ethanol

A

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

B

ethyl 4,4,4-trichloroacetoacetate
3702-98-5

ethyl 4,4,4-trichloroacetoacetate

ethanol
64-17-5

ethanol

chlorocarbonic acid pentachloroethyl ester
97925-35-4

chlorocarbonic acid pentachloroethyl ester

A

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

B

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

ethanol
64-17-5

ethanol

trichloro-acetic acid pentachloroethyl ester
65785-42-4

trichloro-acetic acid pentachloroethyl ester

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

acetaldehyde
75-07-0

acetaldehyde

chloral
75-87-6

chloral

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

Conditions
ConditionsYield
With diethyl ether; aluminum ethoxide
With diethyl ether; magnesium methanolate
With aluminium triisopentylate
acetic acid
64-19-7

acetic acid

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

Conditions
ConditionsYield
With chlorine; phosphorus trichloride im UV-Licht; Behandeln des Reaktionsprodukts mit Aethanol;
aluminum ethoxide
555-75-9

aluminum ethoxide

chloral
75-87-6

chloral

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

Conditions
ConditionsYield
With benzene
aluminum ethoxide
555-75-9

aluminum ethoxide

chloral
75-87-6

chloral

benzene
71-43-2

benzene

A

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

B

2,2,2-trichloroethyl trichloroacetate
13686-37-8

2,2,2-trichloroethyl trichloroacetate

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

Trichloroacetyl chloride
76-02-8

Trichloroacetyl chloride

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

Conditions
ConditionsYield
at 95 - 160℃;
orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

Trichloroacetyl chloride
76-02-8

Trichloroacetyl chloride

A

chloroethane
75-00-3

chloroethane

B

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

C

formic acid ethyl ester
109-94-4

formic acid ethyl ester

Conditions
ConditionsYield
at 160℃; reagiert analog mit anderen Carbonsaeure- und Sulfonsaeurechloriden;
at 95 - 160℃;
ethanol
64-17-5

ethanol

Trichloroacetyl chloride
76-02-8

Trichloroacetyl chloride

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

phosphorus pentachloride
10026-13-8, 874483-75-7

phosphorus pentachloride

oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

acetaldehyde
75-07-0

acetaldehyde

chloral
75-87-6

chloral

magnesium aluminium ethylate

magnesium aluminium ethylate

A

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

B

2,2,2-trichloroethyl trichloroacetate
13686-37-8

2,2,2-trichloroethyl trichloroacetate

C

ethyl acetate
141-78-6

ethyl acetate

D

<2.2.2-trichloro-ethyl>-acetate

<2.2.2-trichloro-ethyl>-acetate

Conditions
ConditionsYield
Prod.5,6,7:2.2.2-Trichlor-aethylalkohol, 3-Hydroxy-1-acetoxy-butan, 4.4.4-Trichlor-3-hydroxy-1-acetoxy-butan;
ethanol
64-17-5

ethanol

trichlorolactic acid tetrachloroethylidene ester

trichlorolactic acid tetrachloroethylidene ester

A

ethyl 3,3,3-trichloro-2-hydroxypropanoate

ethyl 3,3,3-trichloro-2-hydroxypropanoate

B

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

trichloromethyl trichloroacetate
6135-29-1

trichloromethyl trichloroacetate

alcohol (little)

alcohol (little)

A

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

B

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

trichloromethyl trichloroacetate
6135-29-1

trichloromethyl trichloroacetate

alcohol (many)

alcohol (many)

A

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

B

carbonic acid ester

carbonic acid ester

Conditions
ConditionsYield
in Waerme;
ethanol
64-17-5

ethanol

trichlorolactic acid tetrachloroethylidene ester

trichlorolactic acid tetrachloroethylidene ester

A

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

B

trichlorolactic acid ethyl ester

trichlorolactic acid ethyl ester

benzaldehyde
100-52-7

benzaldehyde

1-ethoxyethyl trichloroethanoate

1-ethoxyethyl trichloroethanoate

triethyl phosphite
122-52-1

triethyl phosphite

A

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

B

ethyl 1-(1-ethoxyethyl)benzylphosphonate

ethyl 1-(1-ethoxyethyl)benzylphosphonate

1-ethoxyethyl dichloroethanoate

1-ethoxyethyl dichloroethanoate

triethyl phosphite
122-52-1

triethyl phosphite

A

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

B

diethyl 1-ethoxyethylphosphonate
23081-52-9

diethyl 1-ethoxyethylphosphonate

Conditions
ConditionsYield
at 50 - 80℃; for 4.5h; Title compound not separated from byproducts;
chloral
75-87-6

chloral

A

ethyl 2,2,4,4,4-pentachloro-3-hydroxybutyrate
869769-11-9

ethyl 2,2,4,4,4-pentachloro-3-hydroxybutyrate

B

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

(4aR,5R)-5,9-Bis-(tert-butyl-dimethyl-silanyloxy)-2,3,4,4a,5,8-hexahydro-1H-benzocycloheptene

(4aR,5R)-5,9-Bis-(tert-butyl-dimethyl-silanyloxy)-2,3,4,4a,5,8-hexahydro-1H-benzocycloheptene

(1S,3S,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-2,2-dichloro-tricyclo[6.4.0.01,3]dodec-5-ene

(1S,3S,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-2,2-dichloro-tricyclo[6.4.0.01,3]dodec-5-ene

Conditions
ConditionsYield
With sodium methylate99%
Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

thiophenol
108-98-5

thiophenol

ethyl phenylsulfenylacetate
7605-25-6

ethyl phenylsulfenylacetate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran 1.) r.t., 10 min, 2.) r.t., 10 min;98%
Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

4-Phenyl-1-butene
768-56-9

4-Phenyl-1-butene

C14H17Cl3O2
1393712-30-5

C14H17Cl3O2

Conditions
ConditionsYield
With silicon carbide In chlorobenzene at 200℃; for 1h; Microwave irradiation; regioselective reaction;98%
Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

(Z)-1-methoxy-1,2-diphenylethene
19202-54-1

(Z)-1-methoxy-1,2-diphenylethene

1,1-Dichloro-r-2-methoxy-2,3-c-diphenylcyclopropane
133616-56-5

1,1-Dichloro-r-2-methoxy-2,3-c-diphenylcyclopropane

Conditions
ConditionsYield
With sodium methylate In diethyl ether 1.) -15 deg C, 90 min, 2.) 4 deg C, overnight;95%
Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

hexanoic acid
142-62-1

hexanoic acid

Ethyl hexanoate
123-66-0

Ethyl hexanoate

Conditions
ConditionsYield
With 18-crown-6 ether; potassium carbonate at 90 - 150℃; for 2h;95%
Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

ethyl (Z)-2-chloro-3-cyclohexylacrylate
1012043-68-3

ethyl (Z)-2-chloro-3-cyclohexylacrylate

Conditions
ConditionsYield
With manganese for 5h; Inert atmosphere; Heating; stereoselective reaction;95%
With Rieke-manganese In tetrahydrofuran for 5h; Inert atmosphere; Reflux; optical yield given as %de; stereoselective reaction;95%
With manganese In tetrahydrofuran for 5h; Reflux; Inert atmosphere; stereoselective reaction;95%
Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

norbornene
498-66-8

norbornene

C11H15Cl3O2

C11H15Cl3O2

Conditions
ConditionsYield
ruthenium(II) bis(triphenylphosphine) dichloride In 1,4-dioxane at 75℃; for 24h; Kharasch reaction;94%
Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

endo-10'-<(triisopropylsilyl)oxy>-anti-spiro2,5>undec-3'-ene>
144018-29-1

endo-10'-<(triisopropylsilyl)oxy>-anti-spiro2,5>undec-3'-ene>

4',exo-5'-dichloro-endo-11'-<(triisopropylsilyl)oxy>-anti-spiro2,6>dodec-3'-ene>
144018-30-4

4',exo-5'-dichloro-endo-11'-<(triisopropylsilyl)oxy>-anti-spiro2,6>dodec-3'-ene>

Conditions
ConditionsYield
With sodium methylate In hexane 1) 0 deg C to room temperature, 2) room temperature, 8 h;93%
Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

triethylamine
121-44-8

triethylamine

ethyl N,N-diethyloxamate
5411-58-5

ethyl N,N-diethyloxamate

Conditions
ConditionsYield
With heptamethyl Coβ-perchlorato-cob(II)yrinate; tetrabutylammonium perchlorate In acetonitrile at 20℃; for 3h; Electrolysis;93%
Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

isovaleraldehyde
590-86-3

isovaleraldehyde

ethyl (Z)-2-chloro-5-methylhex-2-enoate
1012043-67-2

ethyl (Z)-2-chloro-5-methylhex-2-enoate

Conditions
ConditionsYield
With manganese In tetrahydrofuran for 5h; Inert atmosphere; Heating; stereoselective reaction;92%
With Rieke-manganese In tetrahydrofuran for 5h; Inert atmosphere; Reflux; optical yield given as %de; stereoselective reaction;92%
With manganese In tetrahydrofuran for 5h; Reflux; Inert atmosphere; stereoselective reaction;92%
Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

(E)-(1aS,7aR,1'aR,7'aS)-3,6,3',6'-Tetramethoxy-1a,2,7,7a,1'a,2',7',7'a-octahydro-[1,1']bi[cyclopropa[b]naphthalenylidene]
179234-15-2, 179466-22-9

(E)-(1aS,7aR,1'aR,7'aS)-3,6,3',6'-Tetramethoxy-1a,2,7,7a,1'a,2',7',7'a-octahydro-[1,1']bi[cyclopropa[b]naphthalenylidene]

C27H28Cl2O4

C27H28Cl2O4

Conditions
ConditionsYield
With sodium methylate In benzene at 0 - 18℃; for 16h;91%
Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

1-methoxy-cyclohex-1-ene
931-57-7

1-methoxy-cyclohex-1-ene

(1α,6α)-7,7-dichloro-1-methoxy<4.1.0>heptane

(1α,6α)-7,7-dichloro-1-methoxy<4.1.0>heptane

Conditions
ConditionsYield
With sodium methylate In pentane 0 deg C to 18 deg C, 16 h;90%
Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

[1,3]-dioxolan-2-one
96-49-1

[1,3]-dioxolan-2-one

Conditions
ConditionsYield
In potassium carbonate; ethylene glycol90%
With dmap In ethylene glycol
dimethylenecyclourethane
497-25-6

dimethylenecyclourethane

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

3-Carboethoxy-2-Oxazolidinone
3206-30-2

3-Carboethoxy-2-Oxazolidinone

Conditions
ConditionsYield
With dmap89%
1-ethenyl-4-methylbenzene
622-97-9

1-ethenyl-4-methylbenzene

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

2,2,4-trichloro-4-phenyl-butyric acid ethyl ester
57196-89-1

2,2,4-trichloro-4-phenyl-butyric acid ethyl ester

Conditions
ConditionsYield
With PS-PEG-PPh2-CP*RuCl2 In water at 60℃; for 9h; Kharasch reaction; Inert atmosphere;89%
Octanal
124-13-0

Octanal

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

ethyl (Z)-2-chlorodec-2-enoate
1059581-48-4

ethyl (Z)-2-chlorodec-2-enoate

Conditions
ConditionsYield
With Rieke-manganese In tetrahydrofuran for 5h; Inert atmosphere; Reflux; optical yield given as %de; stereoselective reaction;89%
With manganese In tetrahydrofuran for 5h; Reflux; Inert atmosphere; stereoselective reaction;89%
Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

1-((1,1-dimethylethyl)dimethylsilyloxy)-1,3-cyclohexadiene

1-((1,1-dimethylethyl)dimethylsilyloxy)-1,3-cyclohexadiene

ethyl 2,2-dichloro-2-(4-oxocyclohex-2-en-1-yl)acetate

ethyl 2,2-dichloro-2-(4-oxocyclohex-2-en-1-yl)acetate

Conditions
ConditionsYield
With N,N,N',N'',N'''-pentamethyldiethylenetriamine; copper(II) bis(trifluoromethanesulfonate); sodium hydrogencarbonate In 1,2-dichloro-ethane at 80℃; for 18h; Inert atmosphere; Sealed tube; regioselective reaction;89%
Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

(3,4-dihydronaphthalen-1-yl)(phenyl)sulfane
68243-21-0

(3,4-dihydronaphthalen-1-yl)(phenyl)sulfane

1,1-dichloro-1a,2,3,7b-tetrahydro-7b-(phenylthio)-1H-cyclopropanaphthalene
126745-21-9

1,1-dichloro-1a,2,3,7b-tetrahydro-7b-(phenylthio)-1H-cyclopropanaphthalene

Conditions
ConditionsYield
88%
Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

2,6,6-trimethyl-1-((trimethylsilyl)oxy)cycloheptene
124355-82-4

2,6,6-trimethyl-1-((trimethylsilyl)oxy)cycloheptene

8,8-dichloro-3,3,7-trimethyl-1-((trimethylsilyl)oxy)bicyclo<5.1.0>octane
124355-98-2

8,8-dichloro-3,3,7-trimethyl-1-((trimethylsilyl)oxy)bicyclo<5.1.0>octane

Conditions
ConditionsYield
With sodium methylate In pentane 1) 0 deg C, 6h, 2) RT, 15h;88%
Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

N-(indolyl-3-imidoyl)guanidine
119294-45-0

N-(indolyl-3-imidoyl)guanidine

2-amino-4-(indolyl-3)-6-trichloromethyl-sym-triazine
169788-30-1

2-amino-4-(indolyl-3)-6-trichloromethyl-sym-triazine

Conditions
ConditionsYield
In ethanol Heating;88%
Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

benzoic acid hex-5-enyl ester
41795-26-0

benzoic acid hex-5-enyl ester

C17H21Cl3O4
1393712-20-3

C17H21Cl3O4

Conditions
ConditionsYield
With silicon carbide In chlorobenzene at 200℃; for 1h; Microwave irradiation; regioselective reaction;88%
Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

6β-methoxy-3α,5-cyclo-5α-androstan-17-one
14425-92-4

6β-methoxy-3α,5-cyclo-5α-androstan-17-one

ethyl 6β-methoxy-20ξ-chloro-17(20)-i-pregnen-21-oate
81477-80-7

ethyl 6β-methoxy-20ξ-chloro-17(20)-i-pregnen-21-oate

Conditions
ConditionsYield
With diethylaluminium chloride; zinc In tetrahydrofuran; hexane at 0℃; for 2h;87%
10-Undecenal
112-45-8

10-Undecenal

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

ethyl (Z)-2-chlorotrideca-2,12-dienoate
1059581-55-3

ethyl (Z)-2-chlorotrideca-2,12-dienoate

Conditions
ConditionsYield
With Rieke-manganese In tetrahydrofuran for 5h; Inert atmosphere; Reflux; optical yield given as %de; stereoselective reaction;87%
With manganese In tetrahydrofuran for 5h; Reflux; Inert atmosphere; stereoselective reaction;87%
styrene
292638-84-7

styrene

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

2,2,4-trichloro-4-phenyl-butyric acid ethyl ester
57196-89-1

2,2,4-trichloro-4-phenyl-butyric acid ethyl ester

Conditions
ConditionsYield
With (η5-1-t-Bu-2-PhC≡C-(1,2-azaboronyl))RuCl(PPh3)2 In toluene at 85℃; for 5h; Schlenk technique; Inert atmosphere; Glovebox;85%
With 2,2'-azobis(isobutyronitrile); Cp*Ru(PPh3)2Cl In (2)H8-toluene at 60℃; for 1.5h; Inert atmosphere;61%
ruthenium(II) bis(triphenylphosphine) dichloride In benzene at 75℃; for 24h; Kharasch reaction;60%
Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

phenylacetylene
536-74-3

phenylacetylene

1,1,1-trichloro-4-phenyl-3-butyn-2-one
66725-82-4

1,1,1-trichloro-4-phenyl-3-butyn-2-one

Conditions
ConditionsYield
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: Ethyl trichloroacetate With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at 20℃; for 2h; Further stages.;
85%
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 3h; Inert atmosphere;
Stage #2: Ethyl trichloroacetate With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere;
83%
(i) nBuLi, (ii) /BRN= 1761567/; Multistep reaction;
Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

C28H52O2Si2

C28H52O2Si2

C23H37ClO2Si

C23H37ClO2Si

Conditions
ConditionsYield
With sodium methylate85%
Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

3-tetrahydropyran-2-yloxy-androst-5-en-17-one
19637-35-5

3-tetrahydropyran-2-yloxy-androst-5-en-17-one

ethyl 20ξ-chloro-3β-(tetrahydropyranyloxy)-5,17(20)-pregnadien-21-oate
81477-79-4

ethyl 20ξ-chloro-3β-(tetrahydropyranyloxy)-5,17(20)-pregnadien-21-oate

Conditions
ConditionsYield
With diethylaluminium chloride; zinc In tetrahydrofuran; hexane at 0℃; for 2h;85%
Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

acetylene
74-86-2

acetylene

1,1,1-trichloro-but-3-yn-2-one

1,1,1-trichloro-but-3-yn-2-one

Conditions
ConditionsYield
Stage #1: acetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: Ethyl trichloroacetate With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at 20℃; for 2h; Further stages.;
85%
1.3-propanedithiol
109-80-8

1.3-propanedithiol

Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

ethyl 1,3-dithiane-2-carboxylate
20462-00-4

ethyl 1,3-dithiane-2-carboxylate

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h;85%

515-84-4Relevant articles and documents

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Sokolskii,Knunjanz

, (1965)

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Alkyl Halides via Visible Light Mediated Dehalogenation

Rathnayake, Manjula D.,Weaver, Jimmie D.

supporting information, p. 9681 - 9687 (2019/11/28)

Net selective bromination and chlorination of activated C-H bonds can be effected in generally high yield via a simple perhalogenation/dehalogenation sequence. The photochemical reductions require no photocatalyst, relying instead on the formation of an electron donor-acceptor complex of the substrate and reductant, or alternatively autophotocatalysis. Some reactions proceed despite any apparent photon absorption, serving as a cautionary tale for other photochemical reactions involving amines. Mechanistic experiments provide an explanation for this observation.

Efficient partial hydrogenation of trichloromethyl to gem-dichloromethyl groups in platinum on carbon-catalyzed system

Sawama, Yoshinari,Imanishi, Takahiro,Nakatani, Ryosuke,Fujiwara, Yuta,Monguchi, Yasunari,Sajiki, Hironao

supporting information, p. 4540 - 4546 (2014/06/10)

While gem-dichloromethyl groups can be directly synthesized by the mono-dechlorination of the corresponding trichloromethyl groups, the suppression control of the over-reduction to form chloromethyl or methyl functionalities is quite difficult. We have established the efficient and widely applicable mono-dechlorination method of the trichloromethyl groups to form the corresponding gem-dichloromethyl groups using platinum on carbon in dimethylacetamide as a specific solvent at 25 °C under a hydrogen atmosphere. The mono-dechlorination of the α,α,α- trichloromethylcarbonyl groups smoothly proceeded by the use of platinum on carbon as a catalyst in a highly chemoselective manner, while the efficient mono-dechlorination of the alkyl- and aryl-trichloromethyl groups required the combined use of Bu3SnH.

Reaction of trialkyl phosphites with monoacylals of dichloro- and trichloroacetic acids

Gazizov,Safina,Khairullin,Gazizov

, p. 313 - 314 (2007/10/03)

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