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4771-80-6 Usage

Chemical Properties

colourless liquid

Check Digit Verification of cas no

The CAS Registry Mumber 4771-80-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,7,7 and 1 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 4771-80:
(6*4)+(5*7)+(4*7)+(3*1)+(2*8)+(1*0)=106
106 % 10 = 6
So 4771-80-6 is a valid CAS Registry Number.
InChI:InChI=1/C7H10O2/c8-7(9)6-4-2-1-3-5-6/h1-2,6H,3-5H2,(H,8,9)/t6-/m1/s1

4771-80-6 Well-known Company Product Price

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  • Alfa Aesar

  • (A15229)  3-Cyclohexene-1-carboxylic acid, 98%   

  • 4771-80-6

  • 5g

  • 807.0CNY

  • Detail
  • Alfa Aesar

  • (A15229)  3-Cyclohexene-1-carboxylic acid, 98%   

  • 4771-80-6

  • 25g

  • 3117.0CNY

  • Detail
  • Alfa Aesar

  • (32676)  3-Cyclohexenecarboxylic acid   

  • 4771-80-6

  • 1g

  • 55.0CNY

  • Detail

4771-80-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-Cyclohexene-1-carboxylic Acid

1.2 Other means of identification

Product number -
Other names Cyclohex-3-enecarboxylic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:4771-80-6 SDS

4771-80-6Synthetic route

buta-1,3-diene
106-99-0

buta-1,3-diene

acrylic acid
79-10-7

acrylic acid

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

Conditions
ConditionsYield
4-tert-Butylcatechol In benzene at 120℃; for 2h; Diels-Alder Reaction;99%
4-tert-Butylcatechol In hexane at 120℃; for 2h; Diels-Alder Reaction;99%
With tetraacetyl diborate In neat (no solvent) at -78 - 20℃; Reagent/catalyst;99%
3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

Conditions
ConditionsYield
With C4H11FeMo6NO24(3-)*3C16H36N(1+); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 8h; Green chemistry;99%
With 4H3N*4H(1+)*CuMo6O18(OH)6(4-); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 12h;99%
With 2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In acetonitrile at 20℃;96%
but-3-enoic acid
625-38-7

but-3-enoic acid

buta-1,3-diene
106-99-0

buta-1,3-diene

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

Conditions
ConditionsYield
With hydroquinone at 240℃; under 3750.38 Torr; Temperature; Autoclave; Inert atmosphere;89.1%
2-(prop-2-enyl)hex-5-enoic acid
112391-51-2

2-(prop-2-enyl)hex-5-enoic acid

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

Conditions
ConditionsYield
Cl2(PCy3)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC6H5 In benzene at 20℃; for 1h;87%
cyclohex-3-enylmethanol
72581-32-9, 1679-51-2

cyclohex-3-enylmethanol

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

Conditions
ConditionsYield
With chromium(VI) oxide; sulfuric acid In acetone at 0℃; Inert atmosphere;83%
With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium chloride; oxygen In 1,2-dichloro-ethane at 25℃; for 48h;81%
With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium chloride; oxygen In 1,2-dichloro-ethane at 20℃; for 48h; Schlenk technique;81%
With manganese(II) bromide; silver carbonate; potassium hydroxide In 1,3,5-trimethyl-benzene at 50 - 165℃; for 20h; Schlenk technique; Inert atmosphere;78%
With ruthenium trichloride; potassium hydroxide; potassium peroxomonosulphate for 6h; Ambient temperature;68%
methyl cyclohex-3-ene-1-carboxylate
6493-77-2

methyl cyclohex-3-ene-1-carboxylate

A

3-cyclohexene-1-methyl 3-cyclohexene-1-carboxylate

3-cyclohexene-1-methyl 3-cyclohexene-1-carboxylate

B

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

C

cyclohex-3-enylmethanol
72581-32-9, 1679-51-2

cyclohex-3-enylmethanol

D

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With hydrogen; sodium methylate; C44H48Cl2N2P2Ru In tetrahydrofuran at 100℃; under 37503.8 Torr; for 2.5h; Product distribution / selectivity; Autoclave;A n/a
B n/a
C 77%
D n/a
With hydrogen; sodium methylate; RuCl2(L-1) In tetrahydrofuran at 80 - 100℃; under 37503.8 Torr; for 2.5 - 5h; Product distribution / selectivity;A n/a
B n/a
C 67%
D n/a
2-exo-aminonorbornan-3-one hydrochloride
24271-57-6, 27852-17-1, 79640-17-8

2-exo-aminonorbornan-3-one hydrochloride

A

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

B

2-hydroxycyclopentylacetic acid
102539-91-3

2-hydroxycyclopentylacetic acid

2-exo-hydroxynorbornan-7-one
5164-69-2, 5164-70-5, 89898-04-4, 97858-70-3

2-exo-hydroxynorbornan-7-one

D

tricyclo<2.2.1.02.6>heptanone
695-05-6

tricyclo<2.2.1.02.6>heptanone

Conditions
ConditionsYield
With sulfuric acid; sodium nitrite In water for 0.666667h;A 6%
B n/a
C 15%
D 3.1%
2-exo-aminonorbornan-3-one hydrochloride
24271-57-6, 27852-17-1, 79640-17-8

2-exo-aminonorbornan-3-one hydrochloride

A

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

2-exo-hydroxynorbornan-7-one
5164-69-2, 5164-70-5, 89898-04-4, 97858-70-3

2-exo-hydroxynorbornan-7-one

C

tricyclo<2.2.1.02.6>heptanone
695-05-6

tricyclo<2.2.1.02.6>heptanone

Conditions
ConditionsYield
With sulfuric acid; sodium nitrite In waterA 6%
B 15%
C 3.1%
2-diazonorbornan-3-one
5169-59-5

2-diazonorbornan-3-one

A

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

B

tricyclo<2.2.1.02.6>heptanone
695-05-6

tricyclo<2.2.1.02.6>heptanone

Conditions
ConditionsYield
With sulfuric acid; sodium nitrite In waterA 36 mg
B 3.6%
2-diazonorbornan-3-one
5169-59-5

2-diazonorbornan-3-one

A

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

2-endo-hydroxynorbornan-3-one
5164-67-0, 5164-68-1, 89898-01-1, 119565-95-6

2-endo-hydroxynorbornan-3-one

2-hydroxybicyclo<3.1.1>heptan-6-one
5597-91-1, 41780-95-4

2-hydroxybicyclo<3.1.1>heptan-6-one

D

tricyclo<2.2.1.02.6>heptanone
695-05-6

tricyclo<2.2.1.02.6>heptanone

Conditions
ConditionsYield
With sulfuric acid In waterA n/a
B n/a
C n/a
D 1%
β-Propiolactone
57-57-8

β-Propiolactone

buta-1,3-diene
106-99-0

buta-1,3-diene

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

Conditions
ConditionsYield
With potassium carbonate
trans-4-bromo-cyclohexanecarboxylic acid
934-66-7

trans-4-bromo-cyclohexanecarboxylic acid

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

Conditions
ConditionsYield
With sodium carbonate
trans-3-Methoxycyclohexanecarboxylic acid
73873-54-8

trans-3-Methoxycyclohexanecarboxylic acid

A

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

B

3-cyclohexenecarboxylic anhydride
40608-18-2

3-cyclohexenecarboxylic anhydride

Conditions
ConditionsYield
With sulfuric acid; acetic anhydride
(+/-)-trans-3-bromo-cyclohexanecarboxylic acid
80552-59-6, 80580-64-9, 101011-80-7

(+/-)-trans-3-bromo-cyclohexanecarboxylic acid

N,N-diethylaniline
91-66-7

N,N-diethylaniline

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

A

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

B

3-hydroxymethylcyclohexene
103668-33-3, 3309-97-5

3-hydroxymethylcyclohexene

Conditions
ConditionsYield
With potassium hydroxide at 70℃;
With potassium hydroxide; sodium hydroxide at 250℃;
ethyl-3-cyclohexene-1-carboxylate
15111-56-5

ethyl-3-cyclohexene-1-carboxylate

A

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

B

ethene
74-85-1

ethene

Conditions
ConditionsYield
Product distribution; Thermodynamic data; Irradiation; Arrhenius parameters, different threshold energies;
4-methoxyphenylthiomethyl 3-cyclohexenecarboxylate
134281-46-2

4-methoxyphenylthiomethyl 3-cyclohexenecarboxylate

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate In water; acetonitrile electrolyse (electrodes of platinum, constant current of 0.1 A); Yield given;
C13H24O2Si

C13H24O2Si

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran Yield given;
2-endo-aminonorbornane-3-one hydrochloride
24271-57-6, 27852-17-1, 79640-17-8

2-endo-aminonorbornane-3-one hydrochloride

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

Conditions
ConditionsYield
With sulfuric acid; sodium nitrite In water for 0.25h;
methyl cyclohex-3-ene-1-carboxylate
6493-77-2

methyl cyclohex-3-ene-1-carboxylate

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

Conditions
ConditionsYield
Hydrolysis;
Stage #1: methyl cyclohex-3-ene-1-carboxylate With water; sodium hydroxide In methanol at 20℃; for 16h;
Stage #2: With hydrogenchloride In methanol; water Product distribution / selectivity;
β-Propiolactone
57-57-8

β-Propiolactone

buta-1,3-diene
106-99-0

buta-1,3-diene

potassium carbonate

potassium carbonate

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

Conditions
ConditionsYield
at 200℃;
'trans'-3-bromo-cyclohexane-carboxylic acid-(1)

'trans'-3-bromo-cyclohexane-carboxylic acid-(1)

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

Conditions
ConditionsYield
With N,N-diethylaniline
(+-)-cyclohex-3-enecarboxylic acid methyl ester

(+-)-cyclohex-3-enecarboxylic acid methyl ester

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

Conditions
ConditionsYield
With sodium hydroxide
With potassium hydroxide
(+-)-cyclohexene-(3)-carbonitrile-(1)

(+-)-cyclohexene-(3)-carbonitrile-(1)

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

Conditions
ConditionsYield
With sodium hydroxide
ethanolic solution of (+-)-cyclohexene-(3)-carbaldehyde-(1)

ethanolic solution of (+-)-cyclohexene-(3)-carbaldehyde-(1)

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

Conditions
ConditionsYield
With potassium hydroxide; silver nitrate
methylammonium carbonate
15719-64-9, 15719-76-3, 97762-63-5

methylammonium carbonate

magnesium compound of 4-bromo-cyclohexene-(1)

magnesium compound of 4-bromo-cyclohexene-(1)

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

Conditions
ConditionsYield
With ethanol
(+-)-1-formyl-cyclohexene-(3)

(+-)-1-formyl-cyclohexene-(3)

A

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

B

cyclohex-3-enylmethanol
72581-32-9, 1679-51-2

cyclohex-3-enylmethanol

Conditions
ConditionsYield
With potassium hydroxide at 65 - 75℃;
trans-4-bromo-cyclohexanecarboxylic acid
934-66-7

trans-4-bromo-cyclohexanecarboxylic acid

natrium carbonate

natrium carbonate

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

(+-)-5c-cyano-2t-methoxy-cyclohexyl-r-mercury(1+) chloride

(+-)-5c-cyano-2t-methoxy-cyclohexyl-r-mercury(1+) chloride

A

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

B

trans-4-methoxycyclohexane-1-carboxylic acid
73873-61-7

trans-4-methoxycyclohexane-1-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide
1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

cyclohex-3-enylmethanol
72581-32-9, 1679-51-2

cyclohex-3-enylmethanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether a) 22 deg C, 12 h, b) reflux, 4 h;100%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;100%
With C25H42N6Rh(1+)*CF3O3S(1-); phenylsilane In tetrahydrofuran at 30℃; for 20h; Inert atmosphere;71%
With lithium aluminium tetrahydride In diethyl ether for 5h; Heating;
1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

methyl iodide
74-88-4

methyl iodide

methyl cyclohex-3-ene-1-carboxylate
6493-77-2

methyl cyclohex-3-ene-1-carboxylate

Conditions
ConditionsYield
With calcium sulfate; silver(l) oxide for 24h;100%
1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

(1RS,4SR,5RS)-4-bromo-6-oxabicyclo<3.2.1>octan-7-one
19903-12-9, 19914-91-1, 90084-76-7, 139893-81-5

(1RS,4SR,5RS)-4-bromo-6-oxabicyclo<3.2.1>octan-7-one

Conditions
ConditionsYield
With bromine; potassium bromide at 150℃; for 3h;99.4%
With trimethylsilyl bromide; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine In chloroform for 12h; Heating;55%
With trimethylsilyl bromide; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine In chloroform for 12h; Heating;55%
With trimethylsilyl bromide; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine In chloroform for 12h; Product distribution; Heating; other unsaturated carboxylic acid; various amines, solvents and reaction times;55%
Multi-step reaction with 2 steps
1: 89 percent / Br2 / CHCl3 / 0.25 h / 20 °C
2: 75 percent / aq. NaOH; phenolphthalein / 0.5 h / 60 °C
View Scheme
1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

Cyclohexanecarboxylic acid
98-89-5

Cyclohexanecarboxylic acid

Conditions
ConditionsYield
With hydrogen; 3% Pd/C In benzene at 100℃; under 6205.94 Torr;99%
With hydrogen; 3% Pd/C In hexane at 100℃; under 6205.94 Torr;99%
With hydrogen; Rhodium chloride tri(triphenylphosphine-meta-trisulfonate) In water for 18h; Ambient temperature;95%
1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

Tetraethylene glycol
112-60-7

Tetraethylene glycol

C22H34O7

C22H34O7

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene Dean-Stark; Large scale;99%
1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

2,2,2,-trichloroethoxycarbonyl azide

2,2,2,-trichloroethoxycarbonyl azide

2,2,2-trichloroethyl cyclohex-3-en-1-ylcarbamate

2,2,2-trichloroethyl cyclohex-3-en-1-ylcarbamate

Conditions
ConditionsYield
With dmap; copper diacetate In acetonitrile at 80℃; for 3h; Schlenk technique; Sealed tube;99%
1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

(+/-)-4-iodo-6-oxabicyclo[3.2.1]octan-7-one
19914-92-2

(+/-)-4-iodo-6-oxabicyclo[3.2.1]octan-7-one

Conditions
ConditionsYield
Stage #1: 1,2,5,6-tetrahydrobenzoic acid With sodium hydrogencarbonate
Stage #2: With iodine; potassium iodide at 20℃; for 16h;
97%
With iodine; sodium hydrogencarbonate; potassium iodide In water at 20℃; for 24h;96%
With iodine; sodium hydrogencarbonate; potassium iodide In water at 20℃; for 16h;96%
1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

phenylselenium trichloride
42572-42-9

phenylselenium trichloride

(4-carboxy-2-chlorocyclohexyl)phenylselenium dichloride
109392-01-0

(4-carboxy-2-chlorocyclohexyl)phenylselenium dichloride

Conditions
ConditionsYield
In diethyl ether at 0℃;97%
1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

methyl iodide
74-88-4

methyl iodide

1-methyl-3-cyclohexenecarboxylic acid
16646-42-7

1-methyl-3-cyclohexenecarboxylic acid

Conditions
ConditionsYield
Stage #1: 1,2,5,6-tetrahydrobenzoic acid With n-butyllithium; bis(dimethylamino)(i-propyl)phosphine oxide; diisopropylamine In tetrahydrofuran; hexane at -20 - 20℃; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran; hexane at -25 - 20℃;
97%
Stage #1: 1,2,5,6-tetrahydrobenzoic acid With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; hexane at -78 - 60℃; for 2.5h;
Stage #2: methyl iodide In tetrahydrofuran; hexane at 20℃;
Stage #1: 1,2,5,6-tetrahydrobenzoic acid With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; hexane at -78 - 60℃; for 2h;
Stage #2: methyl iodide In tetrahydrofuran; hexane
27 g
1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With palladium (II) trifluoroacetate; sodium anthraquinone-2-sulfonate; oxygen; magnesium sulfate In chlorobenzene at 110℃; under 760.051 Torr; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Concentration; Sealed tube;97%
1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

2,3-Dichloro-1-propanol
616-23-9

2,3-Dichloro-1-propanol

Cyclohex-3-enecarboxylic acid 2,3-dichloro-propyl ester
145521-41-1

Cyclohex-3-enecarboxylic acid 2,3-dichloro-propyl ester

Conditions
ConditionsYield
With sulfuric acid In toluene at 130℃;96%
With sulfuric acid In toluene at 90℃; Rate constant;
1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

3-thiabis(4-chlorocyclohexanecarboxylic) acid
362603-58-5

3-thiabis(4-chlorocyclohexanecarboxylic) acid

Conditions
ConditionsYield
With sulfur dichloride In dichloromethane at -40 - 20℃; for 3h;96%
1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

6-oxabicyclo<3.2.1>-oct-3-en-7-one
4720-83-6

6-oxabicyclo<3.2.1>-oct-3-en-7-one

Conditions
ConditionsYield
With iodine; sodium hydrogencarbonate; potassium iodide In water at 20℃;96%
Multi-step reaction with 2 steps
1: 94 percent / NaHCO3, I2/KI / H2O / 21 h / 21 °C
2: 89 percent / DBU / tetrahydrofuran / 16 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: sodium hydrogencarbonate; potassium iodide; iodine / water / 12 h / 20 °C
2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 6 h / 70 °C / Inert atmosphere
View Scheme
1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

benzyl alcohol
100-51-6

benzyl alcohol

(±)-benzyl cyclohex-3-ene-1-carboxylate
91503-67-2

(±)-benzyl cyclohex-3-ene-1-carboxylate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform96%
meta-fluoroaniline
372-19-0

meta-fluoroaniline

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

cyclohex-3-enecarboxylic acid (3-fluoro-phenyl)-amide
263723-89-3

cyclohex-3-enecarboxylic acid (3-fluoro-phenyl)-amide

Conditions
ConditionsYield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane95%
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide Acylation;
1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

racemate-4-iodo-6-oxa-bicyclo[3.2.1]octan-7-one

racemate-4-iodo-6-oxa-bicyclo[3.2.1]octan-7-one

Conditions
ConditionsYield
With iodine; sodium hydrogencarbonate; potassium iodide In dichloromethane; water at 5 - 20℃; for 3h;95%
1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

benzylamine
100-46-9

benzylamine

(+/-)-cyclohex-3-enecarboxylic acid benzylamide

(+/-)-cyclohex-3-enecarboxylic acid benzylamide

Conditions
ConditionsYield
With pentamethoxy tantalum; 1-(Trimethylsilyl)imidazole In neat (no solvent) at 50℃; for 48h; Inert atmosphere; Sealed tube;95%
With benzotriazol-1-ol; 1,2-dichloro-ethane; triethylamine In N,N-dimethyl-formamide at 23℃; for 16h; Inert atmosphere;
1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

(4S)-4-iodo-6-oxabicyclo[3.2.1]octan-7-one

(4S)-4-iodo-6-oxabicyclo[3.2.1]octan-7-one

Conditions
ConditionsYield
Stage #1: 1,2,5,6-tetrahydrobenzoic acid With sodium hydrogencarbonate In water at 20℃;
Stage #2: With iodine; potassium iodide In water at 20℃; Darkness;
95%
1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

benzyloxycarbonyl azide
3422-03-5

benzyloxycarbonyl azide

benzyl N-(cyclohex-3-en-1-yl)carbamate
210574-45-1

benzyl N-(cyclohex-3-en-1-yl)carbamate

Conditions
ConditionsYield
With dmap; copper diacetate In acetonitrile at 80℃; for 3h; Schlenk technique; Sealed tube;95%
1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

(1RS,4RS,5RS)-4-bromo-6-oxabicyclo<3.2.1>octan-7-one
19914-91-1

(1RS,4RS,5RS)-4-bromo-6-oxabicyclo<3.2.1>octan-7-one

Conditions
ConditionsYield
With N-Bromosuccinimide In dichloromethane at 20℃; for 7h; Darkness; Molecular sieve;94%
With lead(IV) acetate; zinc dibromide70%
With lead(IV) acetate; zinc dibromide In 1,2-dimethoxyethane70%
1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

4-bromo-2-cyclohexenecarboxylic acid

4-bromo-2-cyclohexenecarboxylic acid

(1RS,4SR,5RS)-4-bromo-6-oxabicyclo<3.2.1>octan-7-one
19903-12-9, 19914-91-1, 90084-76-7, 139893-81-5

(1RS,4SR,5RS)-4-bromo-6-oxabicyclo<3.2.1>octan-7-one

Conditions
ConditionsYield
With bromine; potassium bromide at 120℃; for 3h;A 4%
B 94%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

1,3-dioxoisoindolin-2-yl cyclohex-3-ene-1-carboxylate

1,3-dioxoisoindolin-2-yl cyclohex-3-ene-1-carboxylate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;94%
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃;73%
With dmap; diisopropyl-carbodiimide In dichloromethane Inert atmosphere; Schlenk technique;68%
1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

N-methoxylamine hydrochloride
593-56-6

N-methoxylamine hydrochloride

O-methyl (+/-)-cyclohex-3-enecarbohydroxamate
53102-82-2

O-methyl (+/-)-cyclohex-3-enecarbohydroxamate

Conditions
ConditionsYield
Stage #1: 1,2,5,6-tetrahydrobenzoic acid With triethylamine In dichloromethane for 0.0833333h; Inert atmosphere;
Stage #2: N-methoxylamine hydrochloride With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 10h; Inert atmosphere;
93%
1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

endo-4-iodo-6-oxabicyclo<3,2,1>octan-7-one
76140-13-1

endo-4-iodo-6-oxabicyclo<3,2,1>octan-7-one

Conditions
ConditionsYield
With sodium hypochlorite solution; acetic acid; sodium iodide In water; acetonitrile at 20℃; for 3h; Reagent/catalyst; Solvent; Temperature;92%
With iodine; sodium hydrogencarbonate; sodium iodide In water at 20℃;89%
With iodine; sodium hydrogencarbonate; potassium iodide In water at 20℃; for 18h;84%
1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

tert-butyl methyl ether
1634-04-4

tert-butyl methyl ether

methyl cyclohex-3-ene-1-carboxylate
6493-77-2

methyl cyclohex-3-ene-1-carboxylate

Conditions
ConditionsYield
With iron(III) trifluoromethanesulfonate at 90℃; Schlenk technique;92%
1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

3,4-Dihydroxycyclohexanecarboxylic acid-γ-lactone
88255-83-8, 116498-92-1, 126873-60-7

3,4-Dihydroxycyclohexanecarboxylic acid-γ-lactone

Conditions
ConditionsYield
With 5,10,15,20-tetra(2',6'-dichlorophenyl)porphyrinatoiron(III) chloride; iodosylbenzene In dichloromethane for 20h; Ambient temperature;91%
Stage #1: 1,2,5,6-tetrahydrobenzoic acid With 3-chloro-benzenecarboperoxoic acid In tetrachloromethane for 4h;
Stage #2: With triethylamine In tetrachloromethane at 65℃; for 4h;
50%
Multi-step reaction with 2 steps
1: m-CPBA / CH2Cl2 / 0 °C
2: chlorobenzene / 130 °C
View Scheme
Multi-step reaction with 2 steps
1: aqueous peroxyformic acid
2: 0.06 Torr
View Scheme
Stage #1: 1,2,5,6-tetrahydrobenzoic acid With 3-chloro-benzenecarboperoxoic acid
Stage #2: With triethylamine
1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

aniline
62-53-3

aniline

N-phenylcyclohex-3-ene-1-carboxamide

N-phenylcyclohex-3-ene-1-carboxamide

Conditions
ConditionsYield
Stage #1: 1,2,5,6-tetrahydrobenzoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 0.25h; Inert atmosphere;
Stage #2: aniline In dichloromethane at 20℃; Inert atmosphere;
91%
Stage #1: 1,2,5,6-tetrahydrobenzoic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
Stage #2: aniline In tetrahydrofuran at 20℃; Inert atmosphere;

4771-80-6Relevant articles and documents

Blattel,Yates

, p. 1073 (1972)

Asymmetric Synthesis of Optically Active 3-Cyclohexene-1-carboxylic Acid Utilizing Lactic Ester as a Chiral Auxiliary in the Diastereoselective Diels–Alder Reaction

Ochiai, Hidenori,Hayashi, Wakana,Nishiyama, Akira,Fujita, Ryunosuke,Kubota, Shunichi,Sasagawa, Miwa,Nishi, Tatsuya

supporting information, p. 1002 - 1009 (2022/02/09)

The optically active 3-cyclohexene-1-carboxylic acid was synthesized through a TiCl4-catalyzed diastereoselective Diels–Alder reaction utilizing lactic acid ester as a chiral auxiliary, which can be removed by washing with H2O. The (S)- and (R)-isomers were both derived from easily available ethyl l-lactate.

Organocatalyzed Aerobic Oxidation of Aldehydes to Acids

Dai, Peng-Fei,Qu, Jian-Ping,Kang, Yan-Biao

supporting information, p. 1393 - 1396 (2019/02/26)

The first example organocatalyzed aerobic oxidation of aldehydes to carboxylic acids in both organic solvent and water under mild conditions is developed. As low as 5 mol % N-hydroxyphthalimide was used as the organocatalyst, and molecular O2 was used as the sole oxidant. No transition metals or hazardous oxidants or cocatalysts were involved. A wide range of carboxylic acids bearing diverse functional groups were obtained from aldehydes, even from alcohols, in high yields.

An Efficient Aerobic Oxidation Protocol of Aldehydes to Carboxylic Acids in Water Catalyzed by an Inorganic-Ligand-Supported Copper Catalyst

Yu, Han,Ru, Shi,Zhai, Yongyan,Dai, Guoyong,Han, Sheng,Wei, Yongge

, p. 1253 - 1257 (2018/02/16)

A method for the aerobic oxidation of aldehydes to carboxylic acids in water by using an inorganic-ligand-supported copper catalyst was developed. This method was performed with the use of atmospheric oxygen as the sole oxidant under extremely mild aqueous conditions, and furthermore, a wide range of aldehydes with various functional groups were tolerated. The copper catalyst could be recycled and used in successive reactions at least six times without any appreciable degradation in performance. This method is operationally simple and avoids the use of high-costing, toxic, air/moisture-sensitive, and commercially unavailable organic ligands. The generality of this method gives it potential to be used on the industrial scale.

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