[ CAS No. 3618-03-9 ] {[proInfo.proName]}

Name: 3618-03-9|cis-Methyl 4-hydroxycyclohexanecarboxylate|98%
Brand: Ambeed
SKU: A938533
Rating: 93 (30 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 3618-03-9

Structure of 3618-03-9 * Storage: {[proInfo.prStorage]}

Please Login or Create an Account to: See VIP prices and availability

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

For Research Only 120K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 3618-03-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 3618-03-9 ]

SDS Specification

Alternatived Products of [ 3618-03-9 ]

Product Details of [ 3618-03-9 ]

CAS No. :	3618-03-9	MDL No. :	MFCD20441962
Formula :	C₈H₁₄O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HYDYVXROZHFTGB-UHFFFAOYSA-N
M.W :	158.20	Pubchem ID :	87117
Synonyms :

Calculated chemistry of [ 3618-03-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.88
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	40.9
TPSA :	46.53 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.79 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.93
Log Po/w (XLOGP3) :	0.67
Log Po/w (WLOGP) :	0.71
Log Po/w (MLOGP) :	0.69
Log Po/w (SILICOS-IT) :	0.89
Consensus Log Po/w :	0.98

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.11
Solubility :	12.3 mg/ml ; 0.0775 mol/l
Class :	Very soluble
Log S (Ali) :	-1.22
Solubility :	9.45 mg/ml ; 0.0598 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.57
Solubility :	42.1 mg/ml ; 0.266 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.53

Safety of [ 3618-03-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P270-P301+P312-P330	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 3618-03-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 3618-03-9 ]
Downstream synthetic route of [ 3618-03-9 ]

[ 3618-03-9 ] Synthesis Path-Upstream 1~4

1
[ 3618-03-9 ]
[ 26845-47-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 23, p. 6309 - 6323
[2] Patent: WO2013/157792, 2013, A1,

2
[ 3618-03-9 ]
[ 6297-22-9 ]

Yield	Reaction Conditions	Operation in experiment
81%	With pyridinium chlorochromate In dichloromethane at 20℃;	The 4-hydroxy methyl ester from above (4.147 g; 26.21 mmol) was dissolved in 150 mL DCM and pyridinium chlorochromate (PCC) (8.476 g; 39.32 mmol) was added. The reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was diluted with ether and decanted. Solvents were removed and the residue was purified by flash column chromatography using 25percent EtOAc in hexanes mixture as eluent. The product was obtained as a colorless oil (3.317 g; 81percent yield).
97.5%	With sodium acetate; pyridinium chlorochromate In dichloromethane	EXAMPLE 2 To 400 ml of dry dichloromethane was added 24 g of oven dried Celite, 11.4 g of sodium acetate and 90.5 g of pyridinium chlorochromate with stirring. An additional 350 ml of methylene chloride was added followed by the addition of 44.5 of of methyl 4-hydroxycyclohexanecarboxylate in 40 ml of dichloromethane with a syringe. After 3.5 hours, 800 ml of ether was added with stirring and the mixture was suction filtered through 250 g of silica gel and the solid was washed four times with ether. The combined filtrates were concentrated to a green oil which was taken up in 150 ml of ether and again suction filtered through 50 g of silica gel and the silica gel was rinsed with ether. The combined filtrates were concentrated to a clear oil which was Kugelrohr distilled at 65°-85° C./ca. 1 mm to yield 42.6 g (97.5percent) of methyl 4-oxocyclohexanecarboxylate. ¹ H MNR (CDCl₃, 60 MHz) δ 3.70 (s, 3H); 2.9-1.8 (9 H).
97.5%	With sodium acetate; pyridinium chlorochromate In dichloromethane	EXAMPLE 2 To 400 ml of dry dichloromethane was added 24 g of oven dried Celite, 11.4 g of sodium acetate and 90.5 g of pyridinium chlorochromate with stirring. An additional 350 ml of methylene chloride was added followed by the addition of 44.5 of of methyl 4-hydroxycyclohexanecarboxylate in 40 ml of dichloromethane with a syringe. After 3.5 hours, 800 ml of ether was added with stirring and the mixture was suction filtered through 250 g of silica gel and the solid was washed four times with ether. The combined filtrates were concentrated to a green oil which was taken up in 150 ml of ether and again suction filtered through 50 g of silica gel and silica gel was rinsed with ether. The combined filtrates were concentrated to a clear oil which was Kugelrohr distilled at 65-85°C/ca. 1 mm to yield 42.6 g (97.5percent) of methyl 4-oxocyclohexanecarboxylate. ¹H MNR (CDCl₃, 60 MHz) δ 3.70 (s, 3H); 2.9-1.8 (9 H).

1.9 g

With sodium acetate; pyridinium chlorochromate In dichloromethane at 20℃; for 7 h;

Step 2: Methyl 4-oxocyclohexanecarboxylate 0.75 g of sodium acetate, 9.92 g of pyridine chlorochromate and 2.4 g of Celite were added to 50 mL of dichloromethane. 4.7 g of the methyl 4-hydroxycyclohexanecarboxylate prepared in step 1 was dissolved in 15 mL of dichloromethane, and then added dropwise to the above mixture at room temperature for 20 minutes, followed by stirring at room temperatrure for 7 hours. After the reaction, the residual solid was removed by filtration, and the organic layer was washed with 100 mL of water. The organic layer was dried by using anhydrous magnesium sulfate, concentrated and then separated by column chromatography (ethyl acetate: n-hexane = 1 :3) to obtain 1.9 g of the title compound. NMR(300MHz, CDC1₃) δ 3.73(s, 3H), 2.79~2.78(m, 1H), 2.50~2.37(m, 4H), 2.22-2.21 (m, 2H), 2.05~2.02(m, 2H).

Reference： [1] Journal of Organic Chemistry, 1991, vol. 56, # 5, p. 1758 - 1763
[2] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 23, p. 6309 - 6323
[3] Tetrahedron, 2006, vol. 62, # 42, p. 10000 - 10004
[4] Patent: US2010/9964, 2010, A1, . Location in patent: Page/Page column 73
[5] Farmaco, Edizione Scientifica, 1984, vol. 39, # 12, p. 1024 - 1037
[6] Bulletin de la Societe Chimique de France, 1969, p. 781 - 787
[7] Canadian Journal of Chemistry, 1982, vol. 60, p. 1996 - 2001
[8] Journal of Organic Chemistry, 1986, vol. 51, # 12, p. 2218 - 2227
[9] Patent: US4954489, 1990, A,
[10] Patent: US4748274, 1988, A,
[11] Patent: EP270843, 1991, B1,
[12] Journal of Medicinal Chemistry, 2010, vol. 53, # 1, p. 481 - 491
[13] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 2376 - 2387
[14] Patent: WO2013/157792, 2013, A1, . Location in patent: Page/Page column 22-23

3
[ 3618-03-9 ]
[ 6297-22-9 ]

Reference： [1] Patent: US3932425, 1976, A,

4
[ 3618-03-9 ]
[ 95233-37-7 ]

Reference： [1] Patent: CN104628555, 2016, B,

Recommend Products

Same Skeleton Products

Related Products

Isomers

Technical Information

• Acids Combine with Acyl Halides to Produce Anhydrides • Acyl Chloride Hydrolysis • Acyl Group Substitution • Add Hydrogen Cyanide to Aldehydes and Ketones to Produce Alcohols • Alcohol Syntheses from Aldehydes, Ketones and Organometallics • Alcohols are Weakly Basic • Alcohols as Acids • Alcohols Convert Acyl Chlorides into Esters • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alcohols React with PX3 • Alcoholysis of Anhydrides • Aldehydes and Ketones Form Hemiacetals Reversibly • Aldol Addition • Alkene Hydration • Alkene Hydration • Amide Hydrolysis • Amide Hydrolysis • Amines Convert Esters into Amides • Anhydride Hydrolysis • Appel Reaction • Arndt-Eistert Homologation • Base-Catalyzed Hydration of α,β -Unsaturated Aldehydes and Ketones • Bouveault-Blanc Reduction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Carbonation of Organometallics • Carboxylate Salt Formation • Carboxylic Acids React with Alcohols to Form Esters • Catalytic Hydrogenation • Chloroalkane Synthesis with SOCI2 • Chromium Reagents for Alcohol Oxidation • Chugaev Reaction • Claisen Condensations Produce β-Dicarbonyl Compounds • Claisen Condensations Produce β-Dicarbonyl Compounds • Complex Metal Hydride Reductions • Convert Esters into Aldehydes Using a Milder Reducing Agent • Convert Haloalkanes into Alcohols by SN2 • Corey-Kim Oxidation • Decarboxylation of 3-Ketoacids Yields Ketones • Decarboxylation of Substituted Propanedioic • Decomposition of Lithium Aluminum Hydride by Protic Solvents • Deprotection of Cbz-Amino Acids • Dess-Martin Oxidation • Ester Cleavage • Ester Hydrolysis • Esters Are Reduced by LiAlH4 to Give Alcohols • Esters Hydrolyze to Carboxylic Acids and Alcohols • Ether Synthesis by Oxymercuration-Demercuration • Ethers Synthesis from Alcohols with Strong Acids • Formation of an Amide from an Amine and a Carboxylic Acid • Formation of an Amide from an Amine and a Carboxylic Acid • Friedel-Crafts Alkylations Using Alcohols • Geminal Diols and Acetals Can Be Hydrolyzed to Carbonyl Compounds • Grignard Reagents Transform Esters into Alcohols • Grignard Reagents Transform Esters into Alcohols • Haloalcohol Formation from an Alkene Through Electrophilic Addition • Halogen and Alcohols Add to Alkenes by Electrophilic Attack • Halogen and Alcohols Add to Alkenes by Electrophilic Attack • Halogenation • Hantzsch Pyridine Synthesis • Heat of Combustion • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hemiaminal Formation from Amines and Aldehydes or Ketones • HIO4 Oxidatively Degrades Vicinal Diols to Give Carbonyl Derivatives • Hunsdiecker-Borodin Reaction • Hydration of the Carbonyl Group • Hydride Reductions • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydroboration-Oxidation • Hydroboration-Oxidation • Hydrolysis of Haloalkanes • Jones Oxidation • Ketones Undergo Mixed Claisen Reactions to Form β-Dicarbonyl Compounds • Martin's Sulfurane Dehydrating Reagent • Mitsunobu Reaction • Moffatt Oxidation • Nitriles Hydrolyze to Carboxylic Acids • Osmium Tetroxide Reacts with Alkenes to Give Vicinal Diols • Osmium TetroxideReacts with Alkenes to Give Vicinal Diols • Oxidation of Alcohols by DMSO • Oxidation of Aldehydes Furnishes Carboxylic Acids • Oxidation of Primary Alcohols Furnishes Carboxylic Acids • Oxymercuration-Demercuration • Passerini Reaction • Peptide Bond Formation with DCC • Periodic Acid Degradation of Sugars • Preparation of Alcohols • Preparation of Alkenes by Dehydration of Alcohols • Preparation of Alkenes by Dehydration of Alcohols • Preparation of Alkoxides with Alkyllithium • Preparation of Amines • Preparation of Carboxylic Acids • Primary Ether Cleavage with Strong Nucleophilic Acids • Reactions of Alcohols • Reactions of Amines • Reactions of Carboxylic Acids • Reactions with Organometallic Reagents • Reduction of an Ester to an Alcohol • Reduction of an Ester to an Aldehyde • Reduction of Carboxylic Acids by LiAlH4 • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Ring Opening of an Oxacyclopropane by Lithium Aluminum Hydride • Ritter Reaction • Schmidt Reaction • Sharpless Olefin Synthesis • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Swern Oxidation • Synthesis of Alcohols from Tertiary Ethers • Synthesis of an Alkyl Sulfonate • The Conversion of Carboxylic Acids into Acyl Halides • The Cycloaddition of Dienes to Alkenes Gives Cyclohexenes • The Nucleophilic Opening of Oxacyclopropanes • Thiazolium Salt Catalysis in Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Transesterification • Ugi Reaction • Use 1,3-dithiane to Prepare of α-Hydroxyketones • Vicinal Anti Dihydroxylation of Alkenes • Williamson Ether Syntheses

Historical Records

Related Functional Groups of
[ 3618-03-9 ]

Aliphatic Cyclic Hydrocarbons

[ 6125-57-1 ]

trans-Methyl 4-hydroxycyclohexanecarboxylate

Similarity: 1.00

[ 37722-82-0 ]

Methyl 3-Hydroxycyclohexanecarboxylate

Similarity: 1.00

[ 113474-25-2 ]

Dimethyl 5-hydroxycyclohexane-1,3-dicarboxylate

Similarity: 1.00

[ 99438-47-8 ]

(1S,3S)-Methyl 3-hydroxycyclohexanecarboxylate

Similarity: 1.00

[ 70144-91-1 ]

(1R,3S)-Methyl 3-hydroxycyclohexanecarboxylate

Similarity: 1.00

Alcohols

[ 17449-76-2 ]

Methyl 4-hydroxycyclohexanecarboxylate

Similarity: 1.00

[ 37722-82-0 ]

Methyl 3-Hydroxycyclohexanecarboxylate

Similarity: 1.00

[ 113474-25-2 ]

Dimethyl 5-hydroxycyclohexane-1,3-dicarboxylate

Similarity: 1.00

[ 99438-47-8 ]

(1S,3S)-Methyl 3-hydroxycyclohexanecarboxylate

Similarity: 1.00

[ 70144-91-1 ]

(1R,3S)-Methyl 3-hydroxycyclohexanecarboxylate

Similarity: 1.00

Esters

[ 6125-57-1 ]

trans-Methyl 4-hydroxycyclohexanecarboxylate

Similarity: 1.00

[ 37722-82-0 ]

Methyl 3-Hydroxycyclohexanecarboxylate

Similarity: 1.00

[ 113474-25-2 ]

Dimethyl 5-hydroxycyclohexane-1,3-dicarboxylate

Similarity: 1.00

[ 99438-47-8 ]

(1S,3S)-Methyl 3-hydroxycyclohexanecarboxylate

Similarity: 1.00

[ 70144-91-1 ]

(1R,3S)-Methyl 3-hydroxycyclohexanecarboxylate

Similarity: 1.00

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	Inquiry	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ item.pr_usastock ]}		{[ item.pr_chinastock ]}	{[ item.pr_remark ]}

Yield	Reaction Conditions	Operation in experiment
81%	With pyridinium chlorochromate; In dichloromethane; at 20℃;	The 4-hydroxy methyl ester from above (4.147 g; 26.21 mmol) was dissolved in 150 mL DCM and pyridinium chlorochromate (PCC) (8.476 g; 39.32 mmol) was added. The reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was diluted with ether and decanted. Solvents were removed and the residue was purified by flash column chromatography using 25percent EtOAc in hexanes mixture as eluent. The product was obtained as a colorless oil (3.317 g; 81percent yield).
	In aqueous sulphuric acid; isopropyl alcohol; acetone;	(a) Methyl 4-oxo-1-cyclohexanecarboxylate A 1M solution of chromium trioxide in dilute aqueous sulphuric acid (17ml) was added dropwise at 20° C. to a stirred solution of methyl 4-hydroxy-1-cyclohexanecarboxylate (4.0g) in acetone (30ml). Excess oxidant was destroyed by adding propan-2-ol dropwise until a green coloration persisted. The solution was then diluted with water and extracted with ether (2x), the combined organic extracts were washed with water and brine, then dried and evaporated. Kugelrohr distillation of the residue afforded the ketoester (3.08g) (W.H. Perkin, jr., J.Chem.Soc., 1904, 416); delta(CDCl3, 90MHz) 1.50-2.60 (8H,m), 2.78 (1H,m), and 3.70 (3H,s).
42.6 g (97.5%)	With sodium acetate; pyridinium chlorochromate; In dichloromethane;	EXAMPLE 2 To 400 ml of dry dichloromethane was added 24 g of oven dried Celite, 11.4 g of sodium acetate and 90.5 g of pyridinium chlorochromate with stirring. An additional 350 ml of methylene chloride was added followed by the addition of 44.5 of of <strong>[3618-03-9]methyl 4-hydroxycyclohexanecarboxylate</strong> in 40 ml of dichloromethane with a syringe. After 3.5 hours, 800 ml of ether was added with stirring and the mixture was suction filtered through 250 g of silica gel and the solid was washed four times with ether. The combined filtrates were concentrated to a green oil which was taken up in 150 ml of ether and again suction filtered through 50 g of silica gel and the silica gel was rinsed with ether. The combined filtrates were concentrated to a clear oil which was Kugelrohr distilled at 65°-85° C./ca. 1 mm to yield 42.6 g (97.5percent) of methyl 4-oxocyclohexanecarboxylate. 1 H MNR (CDCl3, 60 MHz) delta 3.70 (s, 3H); 2.9-1.8 (9 H).

42.6 g (97.5%)	With sodium acetate; pyridinium chlorochromate; In dichloromethane;	EXAMPLE 2 To 400 ml of dry dichloromethane was added 24 g of oven dried Celite, 11.4 g of sodium acetate and 90.5 g of pyridinium chlorochromate with stirring. An additional 350 ml of methylene chloride was added followed by the addition of 44.5 of of <strong>[3618-03-9]methyl 4-hydroxycyclohexanecarboxylate</strong> in 40 ml of dichloromethane with a syringe. After 3.5 hours, 800 ml of ether was added with stirring and the mixture was suction filtered through 250 g of silica gel and the solid was washed four times with ether. The combined filtrates were concentrated to a green oil which was taken up in 150 ml of ether and again suction filtered through 50 g of silica gel and silica gel was rinsed with ether. The combined filtrates were concentrated to a clear oil which was Kugelrohr distilled at 65-85°C/ca. 1 mm to yield 42.6 g (97.5percent) of methyl 4-oxocyclohexanecarboxylate. 1H MNR (CDCl3, 60 MHz) delta 3.70 (s, 3H); 2.9-1.8 (9 H).
1.9 g	With sodium acetate; pyridinium chlorochromate; In dichloromethane; at 20℃; for 7.0h;	Step 2: Methyl 4-oxocyclohexanecarboxylate 0.75 g of sodium acetate, 9.92 g of pyridine chlorochromate and 2.4 g of Celite were added to 50 mL of dichloromethane. 4.7 g of the <strong>[3618-03-9]methyl 4-hydroxycyclohexanecarboxylate</strong> prepared in step 1 was dissolved in 15 mL of dichloromethane, and then added dropwise to the above mixture at room temperature for 20 minutes, followed by stirring at room temperatrure for 7 hours. After the reaction, the residual solid was removed by filtration, and the organic layer was washed with 100 mL of water. The organic layer was dried by using anhydrous magnesium sulfate, concentrated and then separated by column chromatography (ethyl acetate: n-hexane = 1 :3) to obtain 1.9 g of the title compound. NMR(300MHz, CDC13) delta 3.73(s, 3H), 2.79~2.78(m, 1H), 2.50~2.37(m, 4H), 2.22-2.21 (m, 2H), 2.05~2.02(m, 2H).

Yield	Reaction Conditions	Operation in experiment
25.0 g (98%)	With nitrogen; potassium carbonate; In methanol;	EXAMPLE 1 A Parr bottle was charged with 150 ml of methanol and 25 g of methyl 4-hydroxybenzoate was added, then the bottle was flushed with nitrogen, 2.5 g of 5% rhodium on alumina was added and the reaction mixture was pressurized under hydrogen at 3.74 atmospheres for 18 hours with constant shaking. The reaction was then flushed with nitrogen and filtered through diatomaceous earth to remove the catalyst. The diatomaceous earth was rinsed with methanol, being careful not to filter the catalyst to dryness. The filtrates were combined and the methanol was removed under reduced pressure with very gentle heat (ca. 40 C.). The residue of product and alumina was taken up in 200 ml of ether to which 3 g of anhydrous potassium carbonate was added. The precipitated alumina and potassium carbonate were removed by filtration through diatomaceous earth. This was rinsed with ether, the filtrates were combined and the solvent was removed under reduced pressure to yield the crude product. This was bulb-to-bulb distilled on Kugelrohr apparatus at 80-100 C./ca. 1 mm to yield 25.0 g (98%) of methyl 4-hydroxycyclohexanecarboxylate. 1 H NMR (CDCl3, 60 MHz) delta 3.85 (s, 1 H); 3.65 (s, 3 H); 2.50-1.20 (m, 10 H).
25.0 g (98%)	With nitrogen; potassium carbonate; In methanol;	EXAMPLE 1 A Parr bottle was charged with 150 ml of methanol and 25 g of methyl 4-hydroxybenzoate was added, then the bottle was flushed with nitrogen, 2.5 g of 5% rhodium on alumina was added and the reaction mixture was pressurized under hydrogen at 3.74 atmospheres for 18 hours with constant shaking. The reaction was then flushed with nitrogen and filtered through diatomaceous earth to remove the catalyst. The diatomaceous earth was rinsed with methanol, being careful not to filter the catalyst to dryness. The filtrates were combined and the methanol was removed under reduced pressure with very gentle heat (ca. 40C). The residue of product and alumina was taken up in 200 ml of ether to which 3 g of anhydrous potassium carbonate was added. The precipitated alumina and potassium carbonate were removed by filtration through diatomaceous earth. This was rinsed with ether, the filtrates were combined and the solvent was removed under reduced pressure to yield the crude product. This was bulb-to-bulb distilled on Kugelrohr apparatus at 80-100C/ca. 1mm to yield 25.0 g (98%) of methyl 4-hydroxycyclohexanecarboxylate. 1H NMR (CDCl3, 60 MHz) delta 3.85 (s, 1 H); 3.65 (s, 3 H); 2.50-1.20 (m, 10 H).
	With hydrogen;Rh/Al2O3; In methanol; at 120℃; under 90009.0 Torr;	Example B-1 200 g of methyl 4-hydroxybenzoate in 1200 ml of methanol are hydrogenated using 20 g of 5% Ru on Al2O3 (Escat 44) at 120 C./120 bar of hydrogen until no more hydrogen is taken up.For work-up, the mixture is filtered through Celite and concentrated using a rotary evaporator.Yield: 200.6 g (96.5% of theory). Without further purification, the crude product was used for preparing Example C-1.

Yield	Reaction Conditions	Operation in experiment
100%	With 1H-imidazole; In DMF (N,N-dimethyl-formamide); at 20℃; for 5.0h;	To a solution of <strong>[3618-03-9]methyl 4-hydroxycyclohexanecarboxylate</strong> (a cis/trans mixture, 5.00 g, 31.6 mmol) and imidazole (4.30 g, 63.2 mmol) in dimethylformamide (20 ml) was added t-butyldimethylsilyl chloride (5.72 g, 37.9 mmol) at room temperature, and stirred at the same temperature for 5 hours. After completion of the reaction, an ethyl acetate/toluene (1/1) solution and water were added thereto, and the organic layer was collected, dried over sodium sulfate and distilled under reduced pressure to remove the solvent, whereby methyl 4-[tert-butyl(dimethyl)silyl]oxy}cyclohexanecarboxylate (8.66 g, 100percent) was obtained.
93%	With 1H-imidazole; In N,N-dimethyl-formamide; at 20℃; for 14.0h;	[1498] 5.0 g (32 mmol) of <strong>[3618-03-9]methyl 4-hydroxycyclohexanecarboxylate</strong>were initially charged in 100 ml of dimethylformamide.6.7 g (44 mmol) oftert-butyldimethylsilyl chlorideand 4.1 g (60 mmol) of imidazole were then added, and themixture was stirred at RT for another 14 h. The solvent wasremoved under reduced pressure and the residue was taken upin 100 ml of methyl tert-butyl ether and 100 ml of saturatedaqueous sodium bicarbonate solution. The phases were separated,the organic phase was dried over magnesium sulphateand filtered and the solvent was removed under reduced pressure.Yield: 8.1 g (93percent of theory)[1499] GC/MS [Method 9]: R,=4.79 min; MS: m/z=272(Mt.
69%	With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 25℃; for 16.0h;	To a stirred solution of compound 1 (10 g, 63.2 mmol) in DMF (50 mL) were added imidazole (10.7 g, 158 mmol) and TBDMS-Cl (10.6 g, 70.7 mmol) at 0 °C. The reaction mixture was warmed to RT and stirred for 16 h. After consumption of the starting material (by TLC), the reaction was quenched with ice water (50 mL) and extracted with diethyl ether (2 x 50 mL). The combined organic layer was washed with citric acid solution and brine solution. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford crude compound which was purified by column chromatography by eluting with 10percent EtOAc/ hexanes to obtain compound 2 (12 g, 69percent) as oily liquid. (0359) 1H NMR (500MHz, DMSO-d6): delta 3.61 (s, 3H), 3.59 - 3.54 (m, 1H), 2.29-2.20 (m, 1H), 1.90- 1.71 (m, 3H), 1.60-1.46 (m, 5H), 0.86 (s, 9H), 0.02 (s, 6H).

[ CAS No. 3618-03-9 ] {[proInfo.proName]}

Quality Control of [ 3618-03-9 ]

Related Doc. of [ 3618-03-9 ]

Product Details of [ 3618-03-9 ]