65355-29-5

Basic information

• Product Name: 4-(trans-4-Propylcyclohexyl)benzoic acid
• Synonyms: 3PCA;4-propylcyclohexyl acid;Benzoic acid, 4-(trans-4-propylcyclohexyl)-;4-(trans-4-n-Propylcyclohexyl);4-(4-TRANS-N-PROPYLCYCLOHEXYL)BENZOIC ACID;4-(TRANS-4-N-PROPYLCYCLOHEXYL)BENZOIC ACID;4-Propyl Cyclohexyl Benzoic Acid;4-Trans-Propylcyclohexanecarboxylic Acid
• CAS NO: 65355-29-5
• Molecular Formula: C₁₆H₂₂O₂
• Molecular Weight: 246.34
• Product Categories: Liqiud crystal intermediates
• Mol File: 65355-29-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 206°C(lit.)
• Boiling Point: 383.7 °C at 760 mmHg
• Flash Point: 181.9 °C
• Appearance: /
• Density: 1.038 g/cm³
• Vapor Pressure: 1.43E-06mmHg at 25°C
• Refractive Index: 1.527
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.33±0.10(Predicted)
• CAS DataBase Reference: 4-(trans-4-Propylcyclohexyl)benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(trans-4-Propylcyclohexyl)benzoic acid(65355-29-5)
• EPA Substance Registry System: 4-(trans-4-Propylcyclohexyl)benzoic acid(65355-29-5)

Safety Data

• Hazardous Substances Data: 65355-29-5(Hazardous Substances Data)

Usage

Uses

Intermediates of Liquid Crystals

InChI:InChI=1/C16H22O2/c1-2-3-12-4-6-13(7-5-12)14-8-10-15(11-9-14)16(17)18/h8-13H,2-7H2,1H3,(H,17,18)

Synthetic route

trans-4-propyl-(4'-cyanophenyl)cyclohexane (61203-99-4) → 4-(trans-4'-propylcyclohexyl)-benzoic acid (65355-29-5)

Conditions	Yield
With sulfuric acid; water for 5h; Heating;

1-[4-(4-Propyl-cyclohexyl)-phenyl]-ethanone (78531-61-0) → 4-(trans-4'-propylcyclohexyl)-benzoic acid (65355-29-5)

Conditions	Yield
With sodium hydroxide; bromine In 1,4-dioxane at 35 - 40℃; for 3h; Yield given;
With bromine In 1,4-dioxane for 5h;

1-cyclohex-1-enyl-propan-1-one (1655-03-4) → 4-(trans-4'-propylcyclohexyl)-benzoic acid (65355-29-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: AlCl3 / 45 °C 2: hydrazine hydrate / bis-(2-hydroxy-ethyl) ether / or in 1:1 mixture of triethanolamine and glycerol 3: AlCl3 / 1,2-dichloro-ethane / 0.5 h 4: aq. NaOH, Br2 / dioxane / 3 h / 35 - 40 °C View Scheme
Multi-step reaction with 6 steps 1: AlCl3 / 45 °C 2: NaBH4 / propan-1-ol / 4 h / 30 - 35 °C 3: p-toluenesulfonic acid / toluene / Heating 4: H2 / 10percent Pd/C / ethanol 5: AlCl3 / 1,2-dichloro-ethane / 0.5 h 6: aq. NaOH, Br2 / dioxane / 3 h / 35 - 40 °C View Scheme

4-propyl-cyclohexanone (40649-36-3) → 4-(trans-4'-propylcyclohexyl)-benzoic acid (65355-29-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: 2.) 10percent aq. HCl / 1.) diethyl ether, 1 h, heating 2: p-toluenesulfonic acid / toluene / Heating 3: H2 / 10percent Pd/C / ethanol 4: AlCl3 / 1,2-dichloro-ethane / 0.5 h 5: aq. NaOH, Br2 / dioxane / 3 h / 35 - 40 °C View Scheme

phenylmagnesium bromide + monomethyl ether of phenyloxanthranol → 4-(trans-4'-propylcyclohexyl)-benzoic acid (65355-29-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: 2.) 10percent aq. HCl / 1.) diethyl ether, 1 h, heating 2: p-toluenesulfonic acid / toluene / Heating 3: H2 / 10percent Pd/C / ethanol 4: AlCl3 / 1,2-dichloro-ethane / 0.5 h 5: aq. NaOH, Br2 / dioxane / 3 h / 35 - 40 °C View Scheme

1-propionyl-2-chlorocyclohexane (88069-91-4) → 4-(trans-4'-propylcyclohexyl)-benzoic acid (65355-29-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: AlCl3 / 45 °C 2: hydrazine hydrate / bis-(2-hydroxy-ethyl) ether / or in 1:1 mixture of triethanolamine and glycerol 3: AlCl3 / 1,2-dichloro-ethane / 0.5 h 4: aq. NaOH, Br2 / dioxane / 3 h / 35 - 40 °C View Scheme
Multi-step reaction with 6 steps 1: AlCl3 / 45 °C 2: NaBH4 / propan-1-ol / 4 h / 30 - 35 °C 3: p-toluenesulfonic acid / toluene / Heating 4: H2 / 10percent Pd/C / ethanol 5: AlCl3 / 1,2-dichloro-ethane / 0.5 h 6: aq. NaOH, Br2 / dioxane / 3 h / 35 - 40 °C View Scheme

trans-1-(4-hydroxyphenyl)-4-propyl-cyclohexane (81936-33-6) → 4-(trans-4'-propylcyclohexyl)-benzoic acid (65355-29-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / toluene / 2 h / Reflux 1.2: 10 h / 80 °C 2.1: dichloro bis(acetonitrile) palladium(II); 1,2-bis-(diphenylphosphino)ethane; caesium carbonate / 20 h / 70 °C / 52505.3 Torr / Autoclave 3.1: sodium hydroxide / water / 2 h / 70 °C View Scheme

trans-4-propylcyclohexyl ethyl benzoate → 4-(trans-4'-propylcyclohexyl)-benzoic acid (65355-29-5)

Conditions	Yield
With sodium hydroxide In water at 70℃; for 2h;	149.46 g

4-hydroxy-benzaldehyde (123-08-0) + 4-(trans-4'-propylcyclohexyl)-benzoic acid (65355-29-5) → C23H26O3

Conditions	Yield
Stage #1: 4-(trans-4'-propylcyclohexyl)-benzoic acid With thionyl chloride Stage #2: 4-hydroxy-benzaldehyde	87%

4-(trans-4'-propylcyclohexyl)-benzoic acid (65355-29-5) → trans-4-(trans-4'-n-propylcyclohexyl)cyclohexanecarboxylic acid (65355-32-0)

Conditions	Yield
Stage #1: 4-(trans-4'-propylcyclohexyl)-benzoic acid With sodium hydroxide; hydrogen In water at 140 - 150℃; under 22502.3 - 30003 Torr; for 1h; Stage #2: With sodium hydroxide In water at 260 - 280℃; under 22502.3 - 30003 Torr; for 2h; Further stages.;	80%
With pentan-1-ol; sodium Heating;	74%

4-(trans-4'-propylcyclohexyl)-benzoic acid (65355-29-5) + bis{1,9-(4-hydroxyphenyl)nonane} (115914-43-7) → nonane-1,9-diylbis(4,1-phenylene) bis(4-(trans 4-propylcyclohexyl)benzoate)

Conditions	Yield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane for 2h;	72%

4-(trans-4'-propylcyclohexyl)-benzoic acid (65355-29-5) → 4-(trans-4-propylcyclohexyl)benzamide (73163-49-2)

Conditions	Yield
With ammonium hydroxide; thionyl chloride 1) DMF, reflux, 2.5 h; 2) DMF, dioxane; Multistep reaction;
Multi-step reaction with 2 steps 1: SOCl2 / 1 h / Heating 2: 25percent aq. NH4OH View Scheme

4-(trans-4'-propylcyclohexyl)-benzoic acid (65355-29-5) → 4-n-propyl-(4-trans-cyclohexyl)benzoyl chloride (81005-00-7)

Conditions	Yield
With thionyl chloride for 1h; Heating;
With thionyl chloride
With thionyl chloride In benzene for 6h; Heating;

4-(trans-4'-propylcyclohexyl)-benzoic acid (65355-29-5) → [4-(4-Propyl-cyclohexyl)-phenyl]-methanol (93205-73-3)

Conditions	Yield
With lithium aluminium tetrahydride
With lithium aluminium tetrahydride In tetrahydrofuran Heating;
With lithium aluminium tetrahydride In tetrahydrofuran Ambient temperature;

4-(trans-4'-propylcyclohexyl)-benzoic acid (65355-29-5) → trans-4-propyl-(4'-cyanophenyl)cyclohexane (61203-99-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: SOCl2 / 1 h / Heating 2: 25percent aq. NH4OH 3: 56 percent / SOCl2, dimethylformamide / 1.5 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 1) SOCl2; 2) 25 percent aq. NH3 / 1) DMF, reflux, 2.5 h; 2) DMF, dioxane 2: SOCl2 / dimethylformamide / 3 h / 80 °C View Scheme

4-(trans-4'-propylcyclohexyl)-benzoic acid (65355-29-5) → 4-(4-Propyl-cyclohexyl)-benzoic acid 4-cyano-phenyl ester (81930-17-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 / 1 h / Heating 2: 63 percent / pyridine / dimethyl ether / overnight View Scheme

4-(trans-4'-propylcyclohexyl)-benzoic acid (65355-29-5) → trans-4'-propylbi(cyclohexane)-trans-4-carboxylic acid chloride (81945-43-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: aq. NaOH; H2; RNC-5 / H2O / 1 h / 140 - 150 °C / 22502.3 - 30003 Torr 1.2: 80 percent / aq. NaOH / H2O / 2 h / 260 - 280 °C / 22502.3 - 30003 Torr 2.1: SOCl2 / benzene View Scheme

4-(trans-4'-propylcyclohexyl)-benzoic acid (65355-29-5) → 3-methyl-2S-[trans-4-(trans-4-propylcyclohexyl)-cyclohexylcarboxamido]butanoic acid

Conditions	Yield
Multi-step reaction with 3 steps 1.1: aq. NaOH; H2; RNC-5 / H2O / 1 h / 140 - 150 °C / 22502.3 - 30003 Torr 1.2: 80 percent / aq. NaOH / H2O / 2 h / 260 - 280 °C / 22502.3 - 30003 Torr 2.1: SOCl2 / benzene 3.1: aq. NaOH / H2O; dioxane View Scheme

4-(trans-4'-propylcyclohexyl)-benzoic acid (65355-29-5) → 5--2-(p-cyanophenyl)pyrimidine

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 / benzene / 6 h / Heating 2: pyridine / 16 h / 70 °C View Scheme

4-(trans-4'-propylcyclohexyl)-benzoic acid (65355-29-5) → trans,trans-4'-propyl-[1,1'-bicyclohexyl]-4-carbonitrile (65355-35-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 74 percent / amyl alcohol, sodium / Heating 2: 35 percent View Scheme

4-(trans-4'-propylcyclohexyl)-benzoic acid (65355-29-5) → 1-Chloromethyl-4-(4-propyl-cyclohexyl)-benzene (93205-81-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 2: SOCl2, pyridine / Ambient temperature View Scheme

4-(trans-4'-propylcyclohexyl)-benzoic acid (65355-29-5) → C24H27F3

Conditions	Yield
Multi-step reaction with 4 steps 1: lithium aluminum hydride / tetrahydrofuran / Ambient temperature 2: 48 percent hydrobromic acid / 10 h / Heating 3: toluene / 6 h / Heating 4: 1.) butyllithium / 1.) hexan/ether, 2 h, room temperature, 2.) hexane/ether, 4 h, room temperature View Scheme

4-(trans-4'-propylcyclohexyl)-benzoic acid (65355-29-5) → C24H29F3

Conditions	Yield
Multi-step reaction with 5 steps 1: lithium aluminum hydride / tetrahydrofuran / Ambient temperature 2: 48 percent hydrobromic acid / 10 h / Heating 3: toluene / 6 h / Heating 4: 1.) butyllithium / 1.) hexan/ether, 2 h, room temperature, 2.) hexane/ether, 4 h, room temperature 5: hydrogen / 10 percent Pd/C / tetrahydrofuran; ethanol / 48 h / 2844.3 Torr View Scheme

4-(trans-4'-propylcyclohexyl)-benzoic acid (65355-29-5) → 4-cyano-3-fluorophenyl 4-(trans-4-propylcyclohexyl)-benzyl ether

Conditions	Yield
Multi-step reaction with 3 steps 1: LiAlH4 / tetrahydrofuran / Heating 2: 1.) Br2, Ph3P / 1.) MeCN, 0-10 deg C; rt, 1 h; 2.) MeCN, rt, 30 min; 3.) 120 deg C, 15 min 3: K2CO3 / butan-2-one / Heating View Scheme

Upstream product

• 81936-33-6 trans-1-(4-hydroxyphenyl)-4-propyl-cyclohexane 
• 78531-61-0 1-[4-(4-Propyl-cyclohexyl)-phenyl]-ethanone 
• 40649-36-3 4-propyl-cyclohexanone 
• 1655-03-4 1-cyclohex-1-enyl-propan-1-one 
• 124-38-9 carbon dioxide 
• 86579-53-5 1-(trans-4-n-propylcyclohexyl)-4-bromobenzene 
• 71-43-2 benzene 
• 88069-92-5 cis-4-propionyl-1-phenylcyclohexane 
• 88069-93-6 trans-4-propionyl-1-phenylcyclohexane 
• 88069-99-2 1-(4-Phenyl-cyclohexyl)-propan-1-ol 
• 88069-94-7 1-Phenyl-4-propyl-cyclohexanol 
• 61203-94-9 trans-4-propyl-1-phenylcyclohexane 
• 79951-21-6 1-(4-propylcyclohex-1-enyl)benzene 
• 78531-57-4 (4-Propylidene-cyclohexyl)-benzene 

Downstream Products

• 61203-99-4 trans-4-propyl-(4'-cyanophenyl)cyclohexane 
• 81930-17-8 4-(4-Propyl-cyclohexyl)-benzoic acid 4-cyano-phenyl ester 
• 151105-68-9 1-Bromomethyl-4-(4-propyl-cyclohexyl)-benzene 
• 93205-81-3 1-Chloromethyl-4-(4-propyl-cyclohexyl)-benzene 
• 65355-35-3 trans,trans-4'-propyl-[1,1'-bicyclohexyl]-4-carbonitrile 
• 93205-73-3 [4-(4-Propyl-cyclohexyl)-phenyl]-methanol 

Relevant articles and documents

Synthesis method of trans-4-alkyl cyclohexyl benzoic acid

The invention belongs to the field of organic chemical synthesis, and discloses a synthetic method of trans-4-alkyl cyclohexyl benzoic acid. According to the method, trans-4-alkyl cyclohexyl phenol isused as a raw material and reacts with sulfonyl chloride to generate aromatic sulfonate, a carbonyl insertion reaction of aromatic sulfonate is catalyzed by palladium to generate a trans-4-alkyl cyclohexyl benzoate compound with alkyl alcohol, and finally ester hydrolysis is performed to obtain the target product trans-4-alkyl cyclohexyl benzoic acid. The method has the advantages of mild reaction conditions, simple synthesis process, and high yield (up to 90% or above), the catalyst is safe and nontoxic and can be repeatedly used, and the synthesis method is environmentally friendly and canbe easily applied to industrial production.

The Synthesis and Liquid Crystal Behavior of p-Benzotrifluoride Compounds II

Four compounds with the general structure R-X-Y-CH2-CH2-Ph-CF3 were synthesized, where X is a 1,4-disubstituted trans-cyclohexyl ring, Y is a phenyl ring, and R is a n-alkyl group.The synthetic procedure is discussed and the structural assignments were confirmed by NMR spectroscopy.The liquid crystal behavior of these compounds was evaluated by DSC and polarizing microscopy.They might be used in fast switching liquid crystal mixtures.

CONVENIENT SYNTHESIS OF 4-(TRANS-4 prime -N-ALKYLCYCLOHEXYL) BENZOIC ACIDS.

A convenient method of obtaining 4-(trans-4 prime -n-alkylcyclohexyl) benzoic acids from alkanoyl chlorides, cyclohexane and benzene is described. Homologous series of above mentioned acids and their nitriles with alkyl tail 2 to 10 carbon atoms were prepared and temperatures of their phase transitions were determined.