JPH0568455B2 - - Google Patents
Info
- Publication number
- JPH0568455B2 JPH0568455B2 JP59068754A JP6875484A JPH0568455B2 JP H0568455 B2 JPH0568455 B2 JP H0568455B2 JP 59068754 A JP59068754 A JP 59068754A JP 6875484 A JP6875484 A JP 6875484A JP H0568455 B2 JPH0568455 B2 JP H0568455B2
- Authority
- JP
- Japan
- Prior art keywords
- meta
- reaction
- present
- methyl
- solvent
- 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 - Lifetime
Links
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229940100198 alkylating agent Drugs 0.000 claims description 7
- 239000002168 alkylating agent Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 230000002152 alkylating effect Effects 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- -1 alkoxybenzyl alcohol Chemical compound 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000001577 simple distillation Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 1
- MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GXDVEXJTVGRLNW-UHFFFAOYSA-N [Cr].[Cu] Chemical compound [Cr].[Cu] GXDVEXJTVGRLNW-UHFFFAOYSA-N 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Description
本発明はメタ−アルコキシベンジルアルコール
の新規な製造方法に関する。メタ−アルコキシベ
ンジルアルコールは医薬の合成中間体として有用
な物質である。従来この化合物の製造方法として
は、例えばメタ−ニトロベンズアルデヒドを出発
原料とし、メターヒドロキシベンズアルデヒドを
経由する方法などが知られている。しかしながら
これらの方法では、高価な原料を必要とし、工程
が長く、かつ、製品の純度が低いなど好ましくな
い点が多い。このため本発明者らはこれらの問題
点を解決すべく鋭意検討を行なつた結果、工業的
に安価に得られるメタ−ヒドロキシ安息香酸を出
発原料として、短かい工程により高純度のメタ−
アルコキシベンジルアルコールを製造する方法を
見出し、本発明に到達したものである。
すなわち、本発明の要旨は、メターヒドロキシ
安息香酸をアルカリ性物質の存在下アルキル化剤
により二重アルキル化してメタ−アルコキシ安息
香酸アルキルを製造する工程および得られたメタ
−アルコキシ安息香酸アルキルを還元する工程よ
りなることを特徴とするメタ−アルコキシベンジ
ルアルコールの製造方法に関する。
以下、本発明を詳細に説明する。
本発明方法の特徴とするところは、メタ−ヒド
ロキシ安息香酸を出発原料とし、アルカリ性物質
の存在下これをアルキル化剤により、同時にヒド
ロキシル基とカルボキシル基の二重アルキル化を
行ないメタ−アルコキシ安息香酸アルキルを得、
ついでこれを還元してメタ−アルコキシベンジル
アルコールを得る点に存する。メタ−ヒドロキシ
安息香酸のアルキル化に際しては、種々のアルキ
ル化剤が用いられる。アルキル化剤の例として
は、例えば、硫酸ジメチル、炭酸ジメチル、塩化
メチル、臭化メチ、ヨウ化メチル、トルエンスル
ホン酸メチル、等があげられる。またC2ないし
C4の低級アルキル化も同様に行ない得る。ただ
し、一般にヒドロキシル基とカルボキシル基を同
時にアルキル化するのは必らずしも容易ではな
く、条件により一方の官能基のみのアルキル化に
とどまりやすい。しかし、本発明者らの検討の結
果、安価な硫酸ジアルキル、特に硫酸ジメチル
を、アルカリ性物質の存在下で用いると良い結果
が得られることが判明した。あるいはヨウ化メチ
ルのごときハロゲン化アルキルをアルカリ性物質
とともに用いてもよい。アルキル化反応は溶媒の
存在下で行なうのが良い。使用できる溶媒は不活
性なものであればよく、例えばメタノール、アセ
トン、ベンゼン、クロロベンゼン等があげられる
が、特に、ジオキサン等のエーテル系溶媒を用い
ると反応が速やかに進行する。硫酸ジメチルのご
ときアルキル化剤の使用量は当量でも良いが、若
干過剰に用い、未反応原料を残さないようにする
のが好ましい。ハロゲン化アルキルを使用する場
合は、過剰量使用するのが好ましい。アルカリ性
物質としては、アルキル化剤から生成する酸根を
中和できるものであればよく、例えば、水酸化ナ
トリウム、炭酸カリウム、水酸化バリウム等を用
いればよい。反応温度は任意であるが、反応を完
結させるために使用する溶媒の還流温度で行なう
とよい。反応終了後、生成したメタ−アルコキシ
安息香酸アルキルは、抽出等により反応系から分
離し、蒸留により精製・回収される。メタ−アル
コキシ安息香酸アルキルの還元は種々の方法によ
り実施し得る。例えば、還元剤として水素化アル
ミニウムリチウム等を用いても良いが、コストの
点を考慮すると、分子状水素による水添反応によ
るのが好ましい。水添反応には触媒を必要とす
る。触媒としては銅系のもの、例えば銅−クロム
系、銅−亜鉛系等のものが好ましい。反応は液相
で溶媒を用いて行なうのが好ましい。溶媒として
は不活性なものであればよいがメタノール等の低
級アルカノールの使用が好ましい。反応温度は
120℃ないし220℃、より好ましくは160℃ないし
190℃程度がよい。高温では副生物の生成が増加
する。反応圧力は50Kg／cm2ないし300Kg／cm2程度
が良い。原料転化率はなるべく高い方が好まし
く、できれば未反応原料を残存させないように反
応を行なうのがよい。生成物は触媒を別後、蒸
留すれば高純度のメタ−アルコキシベンジルアル
コールが容易に回収される。
本発明方法の利点とするところは、水添生成物
の簡単な蒸留により高純度の製品が容易に得られ
ることにあり、従来法の製品に見られるヘテロ原
子を含んだ除去し難い副生物の残存もない。
以下に本発明方法を実施例により更に具体的に
説明するが、本発明はその要旨を越えない限り、
以下の実施例に限定されるものではない。
実施例 １
メタ−メトキシ安息香酸メチルの合成
ガラス製フラスコにメタ−ヒドロキシ安息香酸
34.53ｇ（0.25モル）、硫酸ジメチル58ml（0.6モ
ル）およびジオキサン250mlを仕込み、撹拌しな
がら25％水酸化ナトリウム水溶液96ｇ（0.6モル）
を30分を要して徐々に滴下した。滴下終了後１時
間加熱還流したのち、生成物をエーテルで抽出
し、エーテル層を希硫酸、希水酸化ナトリウム水
溶液および水で順次洗い、硫酸マグネシウム上で
乾燥したのち、簡単な蒸留塔を用いて蒸留した。
沸点114℃（12mmHg）においてメタ−メトキシ安
息香酸メチル35.45ｇ（0.21モル）が得られた。
収率は85.3％であつた。
実施例 ２〜６
下記表に示す溶媒を用い、実施例１と同様にし
てアルキル化を行つた（実施例３では、NaOH
の代りにK2CO3を使用）。
反応温度は各々の溶媒の還流温度とした。一定
時間後加熱還流を停止し、その時点で生成してい
たメタ−メトキシ安息香酸メチルをガスクロマト
グラフイーにより定着した。結果を下記表に示
す。
The present invention relates to a novel method for producing meta-alkoxybenzyl alcohol. Meta-alkoxybenzyl alcohol is a substance useful as a synthetic intermediate for pharmaceuticals. Conventionally, known methods for producing this compound include, for example, a method in which meta-nitrobenzaldehyde is used as a starting material and meta-hydroxybenzaldehyde is used. However, these methods have many disadvantages such as requiring expensive raw materials, long steps, and low purity products. For this reason, the present inventors have conducted intensive studies to solve these problems, and have found that high-purity meta-hydroxybenzoic acid can be produced in a short process using meta-hydroxybenzoic acid, which can be obtained industrially at low cost, as a starting material.
The present invention was achieved by discovering a method for producing alkoxybenzyl alcohol. That is, the gist of the present invention is a process for producing alkyl meta-alkoxybenzoate by double alkylating meta-hydroxybenzoic acid with an alkylating agent in the presence of an alkaline substance, and reducing the obtained alkyl meta-alkoxybenzoate. The present invention relates to a method for producing meta-alkoxybenzyl alcohol, which comprises the steps of: The present invention will be explained in detail below. The method of the present invention is characterized by using meta-hydroxybenzoic acid as a starting material, which is simultaneously subjected to double alkylation of hydroxyl groups and carboxyl groups with an alkylating agent in the presence of an alkaline substance to produce meta-alkoxybenzoic acid. get alkyl,
The process consists in subsequently reducing this to obtain meta-alkoxybenzyl alcohol. Various alkylating agents are used in alkylating meta-hydroxybenzoic acid. Examples of alkylating agents include dimethyl sulfate, dimethyl carbonate, methyl chloride, methyl bromide, methyl iodide, methyl toluenesulfonate, and the like. Also C 2 or
Lower alkylation of C 4 can be carried out similarly. However, it is generally not always easy to alkylate a hydroxyl group and a carboxyl group at the same time, and depending on the conditions, it is likely that only one functional group will be alkylated. However, as a result of studies conducted by the present inventors, it has been found that good results can be obtained by using inexpensive dialkyl sulfate, particularly dimethyl sulfate, in the presence of an alkaline substance. Alternatively, an alkyl halide such as methyl iodide may be used with an alkaline substance. The alkylation reaction is preferably carried out in the presence of a solvent. The solvent that can be used may be any inert one, such as methanol, acetone, benzene, chlorobenzene, etc., but the reaction proceeds particularly quickly when an ether solvent such as dioxane is used. The alkylating agent such as dimethyl sulfate may be used in an equivalent amount, but it is preferable to use a slight excess so as not to leave unreacted raw materials. When using an alkyl halide, it is preferred to use an excess amount. The alkaline substance may be any substance as long as it can neutralize the acid radicals generated from the alkylating agent, and for example, sodium hydroxide, potassium carbonate, barium hydroxide, etc. may be used. Although the reaction temperature is arbitrary, it is preferable to carry out the reaction at the reflux temperature of the solvent used to complete the reaction. After the reaction is completed, the generated alkyl meta-alkoxybenzoate is separated from the reaction system by extraction or the like, and purified and recovered by distillation. Reduction of alkyl meta-alkoxybenzoates can be carried out in a variety of ways. For example, lithium aluminum hydride or the like may be used as the reducing agent, but in consideration of cost, it is preferable to use a hydrogenation reaction using molecular hydrogen. A catalyst is required for the hydrogenation reaction. The catalyst is preferably copper-based, such as copper-chromium or copper-zinc. Preferably, the reaction is carried out in liquid phase using a solvent. Any inert solvent may be used as the solvent, but lower alkanols such as methanol are preferably used. The reaction temperature is
120°C to 220°C, more preferably 160°C to
A temperature of about 190℃ is best. Higher temperatures increase the formation of by-products. The reaction pressure is preferably about 50Kg/cm 2 to 300Kg/cm 2 . It is preferable that the raw material conversion rate is as high as possible, and if possible, it is preferable to carry out the reaction so that no unreacted raw materials remain. After removing the catalyst, the product is distilled to easily recover highly pure meta-alkoxybenzyl alcohol. The advantage of the process of the present invention is that a high-purity product can be easily obtained by simple distillation of the hydrogenated product, eliminating the heteroatom-containing by-products found in conventional products. There is nothing left. The method of the present invention will be explained in more detail with reference to Examples below, but the present invention does not exceed the gist thereof.
The present invention is not limited to the following examples. Example 1 Synthesis of methyl meta-methoxybenzoate Meta-hydroxybenzoic acid was added to a glass flask.
34.53 g (0.25 mol), dimethyl sulfate 58 ml (0.6 mol) and dioxane 250 ml, and while stirring, add 96 g (0.6 mol) of 25% aqueous sodium hydroxide solution.
was gradually added dropwise over a period of 30 minutes. After heating and refluxing for 1 hour after the completion of the dropwise addition, the product was extracted with ether, and the ether layer was washed successively with dilute sulfuric acid, dilute aqueous sodium hydroxide solution, and water, dried over magnesium sulfate, and then extracted using a simple distillation column. Distilled.
35.45 g (0.21 mol) of methyl meta-methoxybenzoate was obtained at a boiling point of 114 DEG C. (12 mm Hg).
The yield was 85.3%. Examples 2 to 6 Alkylation was carried out in the same manner as in Example 1 using the solvents shown in the table below (in Example 3, NaOH
(using K2CO3 instead of K2CO3 ). The reaction temperature was the reflux temperature of each solvent. After a certain period of time, heating under reflux was stopped, and methyl meta-methoxybenzoate produced at that point was fixed by gas chromatography. The results are shown in the table below.
【表】
実施例 ７
メタ−メトキシベンジルアルコールの製造
500mlのSUS製オートクレーブに実施例１で合
成したメタ−メトキシ安息香酸メチル15.0ｇ
（0.0903モル）、メタノール220mlを仕込み、触媒
として日揮化学製Ｎ−203SD（CuO含量45％、Cr2
O3含量43.5％）2.25ｇを加え、170℃、180Kg／cm2
で３時間水添反応を行つた。冷却後、反応生成物
を取り出し、過後、液を単蒸留した。メタ−
メトキシベンジルアルコールが9.40ｇ（0.068モ
ル）得られた。収率は75.3％であつた。得られた
生成物の純度は99.0％以上であり、ヘテロ原子を
含む物質の混入は認められなかつた。[Table] Example 7 Production of meta-methoxybenzyl alcohol 15.0 g of methyl meta-methoxybenzoate synthesized in Example 1 in a 500 ml SUS autoclave
(0.0903 mol), 220 ml of methanol, and N-203SD manufactured by JGC Chemical (CuO content 45%, Cr 2
Add 2.25g ( O3 content 43.5%), 170℃, 180Kg/ cm2
The hydrogenation reaction was carried out for 3 hours. After cooling, the reaction product was taken out, filtered, and the liquid was subjected to simple distillation. Meta
9.40 g (0.068 mol) of methoxybenzyl alcohol was obtained. The yield was 75.3%. The purity of the obtained product was 99.0% or more, and no substances containing heteroatoms were observed.
Claims (1)
の存在下アルキル化剤により二重アルキル化して
メタ−アルコキシ安息香酸アルキルを製造する工
程および得られたメタ−アルコキシ安息香酸アル
キルを還元する工程よりなることを特徴とする、
メタ−アルコキシベンジルアルコールの製造方
法。1. A method comprising the steps of double alkylating meta-hydroxybenzoic acid with an alkylating agent in the presence of an alkaline substance to produce alkyl meta-alkoxybenzoate, and reducing the obtained alkyl meta-alkoxybenzoate. and
Method for producing meta-alkoxybenzyl alcohol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59068754A JPS60214753A (en) | 1984-04-06 | 1984-04-06 | Production of m-alkoxybenzyl alcohol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59068754A JPS60214753A (en) | 1984-04-06 | 1984-04-06 | Production of m-alkoxybenzyl alcohol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60214753A JPS60214753A (en) | 1985-10-28 |
| JPH0568455B2 true JPH0568455B2 (en) | 1993-09-29 |
Family
ID=13382861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59068754A Granted JPS60214753A (en) | 1984-04-06 | 1984-04-06 | Production of m-alkoxybenzyl alcohol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60214753A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008138457A1 (en) * | 2007-05-10 | 2008-11-20 | Saudi Basic Industries Corporation | Process for preparing alkyl alkoxybenzoates in one step |
-
1984
- 1984-04-06 JP JP59068754A patent/JPS60214753A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60214753A (en) | 1985-10-28 |
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