JPS6312859B2 - - Google Patents
Info
- Publication number
- JPS6312859B2 JPS6312859B2 JP15635479A JP15635479A JPS6312859B2 JP S6312859 B2 JPS6312859 B2 JP S6312859B2 JP 15635479 A JP15635479 A JP 15635479A JP 15635479 A JP15635479 A JP 15635479A JP S6312859 B2 JPS6312859 B2 JP S6312859B2
- Authority
- JP
- Japan
- Prior art keywords
- acetic acid
- dialkoxycyclohexyl
- formula
- lower alkyl
- alkyl group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 150000002168 ethanoic acid esters Chemical class 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 4
- RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical class OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000005907 ketalization reaction Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- -1 orthoformic acid ester Chemical class 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 3
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JDMFXJULNGEPOI-UHFFFAOYSA-N 2,6-dichloroaniline Chemical compound NC1=C(Cl)C=CC=C1Cl JDMFXJULNGEPOI-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229960001193 diclofenac sodium Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- ZKMWHVNPJICREU-UHFFFAOYSA-N ethyl 2-(2,2-diethoxycyclohexyl)acetate Chemical compound CCOC(=O)CC1CCCCC1(OCC)OCC ZKMWHVNPJICREU-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- JGMJQSFLQWGYMQ-UHFFFAOYSA-M sodium;2,6-dichloro-n-phenylaniline;acetate Chemical compound [Na+].CC([O-])=O.ClC1=CC=CC(Cl)=C1NC1=CC=CC=C1 JGMJQSFLQWGYMQ-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は新規な２，２−ジアルコキシシクロヘ
キシル酢酸エステル類及びその製造方法に関する
ものである。さらに詳しくは一般式（）
（式中R1およびR2は低級アルキル基を示す）で
表わされる２，２−ジアルコキシシクロヘキシル
酢酸エステル類及びその製造方法に関するもので
ある。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel 2,2-dialkoxycyclohexyl acetic acid esters and a method for producing the same. For more details, please refer to the general formula () The present invention relates to 2,2-dialkoxycyclohexyl acetic acid esters represented by the formula (wherein R 1 and R 2 represent lower alkyl groups) and a method for producing the same.
本発明の２，２−ジアルコキシシクロヘキシル
酢酸エステル類は、例えば２，６−ジクロルアニ
リンと縮合することにより下式
（式中、R1は低級アルキル基を示す）で表わさ
れる2′，6′−ジクロルフエニルイミノシクロヘキ
サン−２−酢酸エステル類に導くことが出来る。
この化合物はさらに“ジクロフエナツク・ナトリ
ウム”と一般名で呼ばれる抗炎症、鎮痛及び解熱
作用等の薬理作用を有する医薬品へと導くことが
出来る。従つて本発明の２，２−ジアルコキシシ
クロヘキシル酢酸エステル類は医薬品合成の中間
体として重要である。 The 2,2-dialkoxycyclohexyl acetic acid ester of the present invention can be produced by the following formula by condensing it with, for example, 2,6-dichloroaniline. (In the formula, R 1 represents a lower alkyl group) 2',6'-dichlorophenyliminocyclohexane-2-acetic acid esters can be obtained.
This compound can be further developed into a drug with pharmacological effects such as anti-inflammatory, analgesic and antipyretic effects, commonly called "diclofenac sodium". Therefore, the 2,2-dialkoxycyclohexyl acetic acid esters of the present invention are important as intermediates for pharmaceutical synthesis.
一般式（）で表わされる本発明の化合物にお
いて、R1及びR2で示される低級アルキル基は、
特に限定されるものではないが、メチル基エチル
基、プロピル基及びブチル基などの炭素数４迄の
アルキル基であることが好ましい。従つて本発明
の２，２−ジアルコキシシクロヘキシル酢酸エス
テル類は、一般式（）
（式中、R1は低級アルキル基好ましくは炭素数
１から４迄のアルキル基を示す）で表わされるシ
クロヘキサノン−２−酢酸エステルを、一般式
（）
HC（OR2）3 ……（）
（式中、R2は低級アルキル基好ましくは炭素数
１から４迄のアルキル基を示す）で表わされるオ
ルトギ酸エステル類によりケタール化することに
より得られる。 In the compound of the present invention represented by the general formula (), the lower alkyl groups represented by R 1 and R 2 are:
Although not particularly limited, alkyl groups having up to 4 carbon atoms such as methyl, ethyl, propyl, and butyl groups are preferred. Therefore, the 2,2-dialkoxycyclohexyl acetate of the present invention has the general formula () (In the formula, R 1 represents a lower alkyl group , preferably an alkyl group having 1 to 4 carbon atoms). In the formula, R 2 is a lower alkyl group, preferably an alkyl group having 1 to 4 carbon atoms.
本発明の２，２−ジアルコキシシクロヘキシル
酢酸エステル類の合成出発原料となるシクロヘキ
サノン−２−酢酸エステル（）は、例えば文
献、J.Am.Chem.Soc.、79、3504（1957）に記載
の方法により得られる。この化合物から導かれる
ケタールには、下式
で示されるエチレンケタールが紹介されている
が、本発明の２，２−ジアルコキシシクロヘキシ
ル酢酸エステルの如きジアルキルケタール（）
は、文献末記載の化合物である。 Cyclohexanone-2-acetate (), which is the starting material for the synthesis of 2,2-dialkoxycyclohexyl acetate of the present invention, is described, for example, in the literature, J.Am.Chem.Soc., 79, 3504 (1957). obtained by the method. The ketal derived from this compound has the following formula: Although the ethylene ketal represented by
is a compound described at the end of the literature.
ケタール化物である２，２−ジアルコキシシク
ロヘキシル酢酸エステル類（）は、ケトンであ
るシクロヘキサノン−２−酢酸エステル（）と
低級アルコールとを塩化カルシウムや酸性触媒の
存在下で反応させる様な常法によつては、得られ
ないか或は得られても収率が非常に低い。これに
対し、オルトギ酸エステル類（）、例えばオル
トギ酸トリメチルエステル、オルトギ酸トリエチ
ルエステルなどをそれぞれ単独で、あるいは低級
アルコールの存在下で用いた場合には、反応は短
時間で終了し、２，２−ジアルコキシシクロヘキ
シル酢酸エステル類（）の収率も大変良い。ま
たオルトギ酸エステル類（）はシクロヘキサノ
ン−２−酢酸エステル（）に対し１〜２倍モ
ル、好ましくは少過剰量使用する。溶媒は特に必
要としないが、低級アルコール類を使用する場合
にはそれらを過剰に用いて溶媒とするのが有利で
ある。 2,2-Dialkoxycyclohexyl acetate (2), which is a ketal compound, is produced by a conventional method in which cyclohexanone-2-acetate (2), which is a ketone, and a lower alcohol are reacted in the presence of calcium chloride or an acidic catalyst. Therefore, it may not be obtained, or even if it is obtained, the yield is very low. On the other hand, when orthoformic acid esters (), such as orthoformic acid trimethyl ester and orthoformic acid triethyl ester, are used alone or in the presence of a lower alcohol, the reaction completes in a short time, and 2. The yield of 2-dialkoxycyclohexyl acetate () is also very good. The orthoformic acid ester () is used in an amount of 1 to 2 times the mole of the cyclohexanone-2-acetic acid ester (2), preferably in slight excess. A solvent is not particularly required, but when lower alcohols are used, it is advantageous to use them in excess.
また本発明の２，２−ジアルコキシシクロヘキ
シル酢酸エステル類の製造においては酸性触媒の
使用が好ましい。而して使用される酸性触媒とし
ては、例えば塩酸、硫酸、リン酸及びｐ−トルエ
ンスルホン酸等の無機あるいは有機の酸が挙げら
れる。反応温度は０℃からオルトギ酸エステル類
の沸点の間が適当である。これらの条件下では、
反応は通常30分ないし３時間位で終了する。 Further, in the production of the 2,2-dialkoxycyclohexyl acetic acid esters of the present invention, it is preferable to use an acidic catalyst. Examples of the acidic catalyst used include inorganic or organic acids such as hydrochloric acid, sulfuric acid, phosphoric acid, and p-toluenesulfonic acid. The reaction temperature is suitably between 0°C and the boiling point of the orthoformic acid ester. Under these conditions,
The reaction usually completes in about 30 minutes to 3 hours.
このケタール化反応はほぼ定量的に進行するの
で、反応液から触媒や溶媒成分を除去した残留物
は殆んど純品として使用出来る。蒸留により精製
する場合は２，２−ジアルコキシシクロヘキシル
酢酸エステル類（）のある種のものは熱的安定
性がよくないので注意が必要である。なかでもジ
メチルケタールは蒸留中に分解し変質し易い。 Since this ketalization reaction proceeds almost quantitatively, the residue obtained by removing the catalyst and solvent components from the reaction solution can be used almost as a pure product. When purifying by distillation, care must be taken since some 2,2-dialkoxycyclohexyl acetic acid esters () have poor thermal stability. Among these, dimethyl ketal is easily decomposed and deteriorated during distillation.
次に実施例により、本発明をさらに具体的に説
明する。 Next, the present invention will be explained in more detail with reference to Examples.
実施例 １
シクロヘキサノン−２−酢酸エチルエステル
46.1ｇ、オルトギ酸トリエチルエステル44.5ｇお
よびｐ−トルエンスルホン酸0.6ｇとをエチルア
ルコール100ml中に溶解し、60℃で1.5時間加熱
し、さらに１時間加熱還流した。次に反応液を冷
却し、ｐ−トルエンスルホン酸を等モル量のナト
リウムエトキシドで中和し、エチルアルコールを
減圧下に蒸発除去した。残留物にジエチルエーテ
ルを加え、水洗し、無水硫酸ナトリウムで乾燥し
た。乾燥溶液からエーテルを減圧下に蒸発し、残
つた油状物64ｇを0.6〜0.7mmHgの減圧下で蒸留
し、沸点93〜96℃の留分として２，２−ジエトキ
シシクロヘキシル酢酸エチルエステル54.4ｇを得
た。収率は理論値の84.2％であつた。Example 1 Cyclohexanone-2-acetic acid ethyl ester
46.1 g of triethyl orthoformate and 0.6 g of p-toluenesulfonic acid were dissolved in 100 ml of ethyl alcohol, heated at 60° C. for 1.5 hours, and further heated under reflux for 1 hour. Next, the reaction solution was cooled, p-toluenesulfonic acid was neutralized with an equimolar amount of sodium ethoxide, and ethyl alcohol was removed by evaporation under reduced pressure. Diethyl ether was added to the residue, washed with water, and dried over anhydrous sodium sulfate. Ether was evaporated from the dry solution under reduced pressure, and 64 g of the remaining oil was distilled under reduced pressure of 0.6-0.7 mmHg to obtain 54.4 g of 2,2-diethoxycyclohexyl acetic acid ethyl ester as a fraction with a boiling point of 93-96°C. Obtained. The yield was 84.2% of theory.
元素分析値：（C14H26O4として）
Ｃ Ｈ
計算値（％） 69.09 10.14
分析値（％） 69.23 10.03
赤外線吸収スペクトル：cm-1（neat）
2980、2950、2880、1755、1462、1382、1300、
1183、1133、1110、1070、980
核磁気共鳴スペクトル：ppm（ccl4）
1.04〜1.35（9H、多重線）、
1.04〜2.80（11H、多重線）、
3.26〜3.80（4H、多重線）、
3.94〜4.20（2H、四重線）
実施例 ２
塩化水素ガス1.3ｇを含むシクロヘキサノン−
２−酢酸エチルエスエル184.2ｇとオルトギ酸ト
リエチルエステル163.0ｇとを40℃で３時間撹拌
した。次いで反応混合物にベンゼン１を加え、
希重ソウ水および水で順次洗浄し、無水硫酸ナト
リウムで乾燥した。乾燥液からベンゼンを留去
後、残留物を減圧蒸留して２，２−ジエトキシシ
クロヘキシル酢酸エチルエステル211.9ｇを得た。Elemental analysis value: (as C 14 H 26 O 4 ) C H Calculated value (%) 69.09 10.14 Analysis value (%) 69.23 10.03 Infrared absorption spectrum: cm -1 (neat) 2980, 2950, 2880, 1755, 1462, 1382 ,1300,
1183, 1133, 1110, 1070, 980 Nuclear magnetic resonance spectrum: ppm (ccl 4 ) 1.04-1.35 (9H, multiplet), 1.04-2.80 (11H, multiplet), 3.26-3.80 (4H, multiplet), 3.94 ~4.20 (2H, quartet) Example 2 Cyclohexanone containing 1.3 g of hydrogen chloride gas
184.2 g of 2-ethyl acetate and 163.0 g of triethyl orthoformate were stirred at 40°C for 3 hours. Then add 1 part of benzene to the reaction mixture,
It was washed successively with dilute sodium chloride solution and water, and dried over anhydrous sodium sulfate. After distilling off benzene from the dry liquid, the residue was distilled under reduced pressure to obtain 211.9 g of ethyl 2,2-diethoxycyclohexyl acetate.
実施例 ３
シクロヘキサノン−２−酢酸メチルエステル
34.0ｇとオルトギ酸トリメチルエステル25.5ｇお
よび濃塩酸1.0ｇとをメチルアルコール100ml中に
溶解し、還流下に２時間加熱した。反応液からメ
チルアルコールおよび未反応原料とを留去した
後、残留物にジエチルエーテルを加え希重ソウ水
および水で順次洗浄し、無水硫酸ナトリウムで乾
燥した。乾燥液からジエチルエーテルを減圧下に
除去し残分として２，２−ジメトキシシクロヘキ
シル酢酸メチルエステル41.1ｇを得た（このもの
は減圧蒸留により変質する傾向があつた）。Example 3 Cyclohexanone-2-acetic acid methyl ester
34.0 g, 25.5 g of trimethyl orthoformate and 1.0 g of concentrated hydrochloric acid were dissolved in 100 ml of methyl alcohol and heated under reflux for 2 hours. After distilling off methyl alcohol and unreacted raw materials from the reaction solution, diethyl ether was added to the residue, which was washed successively with dilute sodium chloride water and water, and dried over anhydrous sodium sulfate. Diethyl ether was removed from the dried liquid under reduced pressure to obtain 41.1 g of 2,2-dimethoxycyclohexyl acetic acid methyl ester as a residue (this product had a tendency to deteriorate during vacuum distillation).
赤外線吸収スペクトル：cm-1（neat）
2960、2870、2840、1755、1450、1305、1180、
1120、1070、950
核磁気共鳴スペクトル：ppm（ccl4）
1.1〜2.8（11H、多重線）、
3.08（3H、一重線）、
3.13（3H、一重線）、
3.60（3H、一重線）
実施例 ４
濃硫酸0.7ｇを用いて実施例３に準じて行ない
２，２−ジメトキシシクロヘキシル酢酸メチルエ
ステル37.8ｇを得た。Infrared absorption spectrum: cm -1 (neat) 2960, 2870, 2840, 1755, 1450, 1305, 1180,
1120, 1070, 950 Nuclear magnetic resonance spectrum: ppm (ccl 4 ) 1.1-2.8 (11H, multiplet), 3.08 (3H, singlet), 3.13 (3H, singlet), 3.60 (3H, singlet) Examples 4 The procedure was carried out according to Example 3 using 0.7 g of concentrated sulfuric acid to obtain 37.8 g of 2,2-dimethoxycyclohexyl acetic acid methyl ester.
Claims (1)
表わされる２，２−ジアルコキシシクロヘキシル
酢酸エステル類。 ２ 一般式（） （式中、R1は低級アルキル基を示す）で表わさ
れるシクロヘキサノン−２−酢酸エステルを一般
式（） HC（OR2）3 （） （式中、R2は低級アルキル基を示す）で表わさ
れるオルトギ酸エステル類によりケタール化する
ことを特徴とする一般式（） （式中、R1及びR2は低級アルキル基を示す）で
表わされる２，２−ジアルコキシシクロヘキシル
酢酸エステル類の製造方法。[Claims] 1 General formula () 2,2-dialkoxycyclohexyl acetic acid esters represented by (wherein R 1 and R 2 represent lower alkyl groups). 2 General formula () (In the formula, R 1 represents a lower alkyl group) Cyclohexanone-2-acetic ester is represented by the general formula () HC(OR 2 ) 3 () (In the formula, R 2 represents a lower alkyl group) General formula () characterized by ketalization with orthoformic acid esters A method for producing a 2,2-dialkoxycyclohexyl acetic acid ester represented by the formula (wherein R 1 and R 2 represent a lower alkyl group).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15635479A JPS5679643A (en) | 1979-12-04 | 1979-12-04 | 2,2-dialkoxycyclohexyl acetate and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15635479A JPS5679643A (en) | 1979-12-04 | 1979-12-04 | 2,2-dialkoxycyclohexyl acetate and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5679643A JPS5679643A (en) | 1981-06-30 |
| JPS6312859B2 true JPS6312859B2 (en) | 1988-03-23 |
Family
ID=15625915
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15635479A Granted JPS5679643A (en) | 1979-12-04 | 1979-12-04 | 2,2-dialkoxycyclohexyl acetate and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5679643A (en) |
-
1979
- 1979-12-04 JP JP15635479A patent/JPS5679643A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5679643A (en) | 1981-06-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4107439A (en) | Process for preparing arylalkanoic acid derivatives | |
| DeTar et al. | Diacyl Peroxide Reactions. III. The Behavior of the Optically Active 3-Phenyl-2-propyl Free Radical1 | |
| JPS6312859B2 (en) | ||
| JPS6412261B2 (en) | ||
| US4016196A (en) | Butenoic and pyruvic acid derivatives | |
| JPS5949207B2 (en) | Diene manufacturing method | |
| JPS584699B2 (en) | Substituted phenylacetic acid derivatives and their production method | |
| US2349795A (en) | Derivatives of 2,4-oxazolidinedione | |
| JPS60112738A (en) | Production of glyoxylic acid ester | |
| JPS6377868A (en) | Alpha-(omega-hydroxyalkyl)furfuryl alcohol and production thereof | |
| US4426536A (en) | Synthesis of phenylacetic acid esters | |
| US2509199A (en) | Pharmaceutical intermediates and process of preparing the same | |
| JPS5855129B2 (en) | Method for producing 2-substituted or unsubstituted geranyl acetates | |
| Manske et al. | A Synthesis of α-Naphthyl-Acetic Acid and Some Homologues | |
| JPS6034940B2 (en) | Fluoromalonic acid derivatives and their production method | |
| US3507907A (en) | Process of producing beta-alkoxy crotonic acid esters | |
| US2540307A (en) | 3, 4-diethoxymandelic acid and process for preparing same | |
| JPH1112208A (en) | Purification of 1,3-dichloropropanol | |
| JP3777407B2 (en) | Method for producing carboxylic acid derivative | |
| US4096338A (en) | Butenoic and pyruvic acid derivatives | |
| SU149419A1 (en) | Method for preparing dichloroacetic acid esters | |
| JP2514001B2 (en) | Method for producing acetin | |
| JPS6034941B2 (en) | Production method of fluoromalonate ester | |
| JPH0528693B2 (en) | ||
| KR890003259B1 (en) | Process for the preparation of bromo fluoro acetic acids |