JPS5822136B2 - Method for producing 3-hydroxy-4-methoxybenzaldehyde compound - Google Patents
Method for producing 3-hydroxy-4-methoxybenzaldehyde compoundInfo
- Publication number
- JPS5822136B2 JPS5822136B2 JP6949479A JP6949479A JPS5822136B2 JP S5822136 B2 JPS5822136 B2 JP S5822136B2 JP 6949479 A JP6949479 A JP 6949479A JP 6949479 A JP6949479 A JP 6949479A JP S5822136 B2 JPS5822136 B2 JP S5822136B2
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- methoxybenzaldehyde
- yield
- compound
- producing
- 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
- -1 3-hydroxy-4-methoxybenzaldehyde compound Chemical class 0.000 title claims description 16
- JVTZFYYHCGSXJV-UHFFFAOYSA-N isovanilline Natural products COC1=CC=C(C=O)C=C1O JVTZFYYHCGSXJV-UHFFFAOYSA-N 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 8
- PCYGLFXKCBFGPC-UHFFFAOYSA-N 3,4-Dihydroxy hydroxymethyl benzene Natural products OCC1=CC=C(O)C(O)=C1 PCYGLFXKCBFGPC-UHFFFAOYSA-N 0.000 claims description 6
- IBGBGRVKPALMCQ-UHFFFAOYSA-N 3,4-Dihydroxybenzaldehyde Natural products OC1=CC=C(C=O)C=C1O IBGBGRVKPALMCQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- NVLTWXMZECWWPC-UHFFFAOYSA-N 3-hydroxy-4,5-dimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(O)=C1OC NVLTWXMZECWWPC-UHFFFAOYSA-N 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- KCDXJAYRVLXPFO-UHFFFAOYSA-N syringaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1O KCDXJAYRVLXPFO-UHFFFAOYSA-N 0.000 description 4
- COBXDAOIDYGHGK-UHFFFAOYSA-N syringaldehyde Natural products COC1=CC=C(C=O)C(OC)=C1O COBXDAOIDYGHGK-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 description 2
- RRKMWVISRMWBAL-UHFFFAOYSA-N 3,4-dihydroxy-5-methoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(O)=C1O RRKMWVISRMWBAL-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- XBGHSBRNXBJICG-UHFFFAOYSA-N 2,3-dimethoxy-5-methylphenol Chemical compound COC1=CC(C)=CC(O)=C1OC XBGHSBRNXBJICG-UHFFFAOYSA-N 0.000 description 1
- OWZZRUPQHSLPPI-UHFFFAOYSA-N 3-ethoxy-4,5-dihydroxybenzaldehyde Chemical compound CCOC1=CC(C=O)=CC(O)=C1O OWZZRUPQHSLPPI-UHFFFAOYSA-N 0.000 description 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N Anisaldehyde Natural products COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 description 1
- 235000017471 coenzyme Q10 Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 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、３，４−ジヒドロキシベンズアルデヒド化合
物の４位の水酸基を選択的にモノメチル化して３−ヒド
ロキシ−４−メトキシベンズアルデヒド化合物を製造す
る方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing a 3-hydroxy-4-methoxybenzaldehyde compound by selectively monomethylating the hydroxyl group at the 4-position of the 3,4-dihydroxybenzaldehyde compound.
３−ヒドロキシ−４−メトキシベンズアルデヒド化合物
は、医薬、農薬等の中間体として有用でノあり、特に３
−ヒドロキシ−４，５−ジメトキシベンズアルデヒドは
、これを水素還元して３−ヒドロキシ−４，５−ジメト
キシトルエンを得、ついでこれを酸化して２，３−ジメ
トキシ−５−メチル−１，４−ベンゾキノンを得ること
ができ、近時生化１学的に注目されている補酵素Ｑ同族
体の合成原料として有用であることが知られている。3-Hydroxy-4-methoxybenzaldehyde compounds are useful as intermediates for pharmaceuticals, agricultural chemicals, etc.
-Hydroxy-4,5-dimethoxybenzaldehyde is hydrogen-reduced to obtain 3-hydroxy-4,5-dimethoxytoluene, which is then oxidized to 2,3-dimethoxy-5-methyl-1,4- It is known that benzoquinone can be obtained and is useful as a raw material for the synthesis of coenzyme Q homologs, which have recently attracted attention in biochemistry.
従来、３−ヒドロキシ−４−メトキシベンズアルデヒド
化合物、特に３−ヒドロキシ−４，５−ジメトキシベン
ズアルデヒドは、３，４−ジヒドロキ；シー５−メトキ
シベンズアルデヒドと等モルの水酸化カリウム水溶液及
び等モルのジメチル硫酸を反応させて得られることが知
られているが、目的生成物以外に３．４．５−１−ジメ
トキシベンズアルデヒド及びシリンガアルデヒド等が多
量に副生する’ （Ｊ、Ａｍｅｒ、Ｃｎｅｍ、Ｓｏｃ、
、 ７４．４２６２ （１９５２）参照〕ので有利で
はなかった。Conventionally, 3-hydroxy-4-methoxybenzaldehyde compounds, particularly 3-hydroxy-4,5-dimethoxybenzaldehyde, have been prepared using 3,4-dihydroxy-5-methoxybenzaldehyde, equimolar potassium hydroxide aqueous solution and equimolar dimethyl sulfate. However, in addition to the desired product, large amounts of 3.4.5-1-dimethoxybenzaldehyde and syringaldehyde are produced as by-products (J, Amer, Cnem, Soc,
, 74.4262 (1952)], so it was not advantageous.
ソコで、本発明者らは、３，４−ジヒドロキシベンズア
ルデヒド化合物の４位の水酸基が選択的にモノメチル化
される条件について種々検討した結果、本発明に到達し
た。The present inventors conducted various studies on the conditions under which the hydroxyl group at the 4-position of a 3,4-dihydroxybenzaldehyde compound is selectively monomethylated, and as a result, they arrived at the present invention.
すなわち、本発明は、一般式；
（ただし、式中のＲは水素原子又はアルコキシ基を示す
）で表わされる３、４−ジヒドロキシベンズアルデヒド
化合物１モルに対してジメチル硫酸を１〜１．２モルの
割合で加え、炭酸ナトリウムの存在下に非プロトン性極
性溶媒中で反応させることを特徴とする、一般式；
（ただし、式中のＲは前記と同じ意味を有する）で表わ
される３−ヒドロキシ−４−メトキシベンズアルデヒド
化合物の製法に関するものである。That is, the present invention provides dimethyl sulfuric acid in an amount of 1 to 1.2 mol per mol of a 3,4-dihydroxybenzaldehyde compound represented by the general formula; 3-hydroxy-, represented by the general formula; The present invention relates to a method for producing a 4-methoxybenzaldehyde compound.
本発明の方法に使用する前記一般式は）で表わされる３
、４−ジヒドロキシベンズアルデヒド化合物として、３
，４−ジヒドロキシベンズアルデヒド、３．４−ジヒド
ロキシ−５−メトキシベンズアルデヒド、３，４−ジヒ
ドロキシ−５−エトキシベンズアルデヒド、３，４−ジ
ヒドロキシ−５−プロポキシベンズアルデヒド等が挙げ
られる。The general formula used in the method of the present invention is represented by 3
, 3 as a 4-dihydroxybenzaldehyde compound
, 4-dihydroxybenzaldehyde, 3,4-dihydroxy-5-methoxybenzaldehyde, 3,4-dihydroxy-5-ethoxybenzaldehyde, 3,4-dihydroxy-5-propoxybenzaldehyde, and the like.
また本発明の方法に使用するジメチル硫酸の使用割合は
、３，４−ジヒドロキシベンズアルデヒド化合物１モル
に対して１〜１．２モルが好ましい。The proportion of dimethyl sulfuric acid used in the method of the present invention is preferably 1 to 1.2 moles per mole of the 3,4-dihydroxybenzaldehyde compound.
この量より多く使用すると３，４−ジヒドロキシベンズ
アルデヒド化合物の３位及び４位の水酸基が両方ともメ
チル化されるか、あるいは３位の水酸基がメチル化され
るので好ましくない。If more than this amount is used, both the 3- and 4-position hydroxyl groups of the 3,4-dihydroxybenzaldehyde compound will be methylated, or the 3-position hydroxyl group will be methylated, which is not preferable.
さらに本発明の方法に使用するアルカリ剤は炭酸ナトリ
ウムであり、その使用割合は、通常、使用するジメチル
硫酸に対して等モル以上使用するのが好ましい。Further, the alkaline agent used in the method of the present invention is sodium carbonate, and it is usually preferable to use it in an amount equal to or more than the same mole relative to the dimethyl sulfate used.
本発明の反応は、アセトン、ジメチルスルホキシド、ジ
オキサン等のような非プロトン性極性溶媒中で行われ、
水溶液中では副反応が生起する。The reaction of the present invention is carried out in an aprotic polar solvent such as acetone, dimethyl sulfoxide, dioxane, etc.
Side reactions occur in aqueous solutions.
反応温度は室温〜１５１°Ｃの範囲が適当であり、通常
、溶媒の還流温度付近が好ましい。The reaction temperature is suitably in the range of room temperature to 151°C, and is usually preferably around the reflux temperature of the solvent.
本発明の方法によって得られる前記一般式（ＩＩ）で表
わされる３−ヒドロキシ−４−メトキシベンズアルデヒ
ド化合物として、３−ヒドロキシ−４−メトキシベンズ
アルデヒド、３−ヒドロキシ−４，５−ジメトキシベン
ズアルデヒド、３−ヒドロキシ−４−メトキシ−５−エ
トキシベンズアルデヒド、３−ヒドロキシ−４−メトキ
シ−５−プロポキシベンズアルデヒド等が挙げられる。As the 3-hydroxy-4-methoxybenzaldehyde compound represented by the general formula (II) obtained by the method of the present invention, 3-hydroxy-4-methoxybenzaldehyde, 3-hydroxy-4,5-dimethoxybenzaldehyde, 3-hydroxy -4-methoxy-5-ethoxybenzaldehyde, 3-hydroxy-4-methoxy-5-propoxybenzaldehyde and the like.
以上、本発明の方法を実施することによって、３．４−
ジヒドロキシベンズアルデヒド化合物の４位の水酸基が
選択的にモノメチル化された３−ヒドロキシ−４−メト
キシベンズアルデヒド化合物を得ることができる。As described above, by implementing the method of the present invention, 3.4-
A 3-hydroxy-4-methoxybenzaldehyde compound in which the hydroxyl group at the 4-position of the dihydroxybenzaldehyde compound is selectively monomethylated can be obtained.
実施例 １
３．４−ジヒドロキシ−５−メトキシベンズアルデヒド
７、６９ （４５ｍｍｏｌ）、ジメチル硫酸６．７ｇ（
５３ｍｍｏｌ）及び炭酸ナトリウム６、 Ｏｉ （５７
ｍｍｏｌ）２をアセトン８０Ｔｔｌ中に加え、４時間、
還流温度で反応させた。Example 1 3.4-dihydroxy-5-methoxybenzaldehyde 7,69 (45 mmol), dimethyl sulfate 6.7 g (
53 mmol) and sodium carbonate 6, Oi (57
mmol)2 in 80 Ttl of acetone for 4 hours.
The reaction was carried out at reflux temperature.
反応終了後、生成物をｐ別したＰ液を濃縮し、力性ソー
ダ水溶液に溶解し、この溶液をトルエンで洗浄して３，
４．５−トリメトキシベンズアルデヒドを除去した。After the reaction was completed, the P solution from which the product had been separated was concentrated, dissolved in aqueous sodium hydroxide solution, and this solution was washed with toluene.
4.5-Trimethoxybenzaldehyde was removed.
ついで前記水溶液を塩：酸で中和後、エーテルで抽出し
、抽出物を減圧蒸留して３−ヒドロキシ−４，５−ジメ
トキシベンズアルデヒド６．９．９（収率８４１％）を
得た。The aqueous solution was then neutralized with salt:acid, extracted with ether, and the extract was distilled under reduced pressure to obtain 6.9.9% of 3-hydroxy-4,5-dimethoxybenzaldehyde (yield: 841%).
融点は６１°Ｃであった。The melting point was 61°C.
なお、３，４．５−トリメトキシベンズアルデヒドの収
率は１０係、シリンガアルデ・ヒトの収率は３％であっ
た。The yield of 3,4.5-trimethoxybenzaldehyde was 10%, and the yield of syringaldehyde was 3%.
実施例 ２
溶媒をアセトンからジメチルスルホキシドに替えた以外
は実施例１と同様に１００’Ｃで２時間反応させた。Example 2 A reaction was carried out at 100'C for 2 hours in the same manner as in Example 1 except that the solvent was changed from acetone to dimethyl sulfoxide.
反応生成物をガスクロマトグラフ分析した。The reaction product was analyzed by gas chromatography.
３−ヒドロキシ−４，５−ジメトキシベンズアルデヒド
の収率は８３係であった。The yield of 3-hydroxy-4,5-dimethoxybenzaldehyde was 83%.
実施例 ３
溶媒をアセトンからジオキサンに替えた以外は実施例１
と同様に反応させた。Example 3 Example 1 except that the solvent was changed from acetone to dioxane
reacted in the same way.
反応生成物をガスクロマトグラフ分析した。The reaction product was analyzed by gas chromatography.
３−ヒドロキシ−４，５−ジメトキシベンズアルデヒド
の収率は７９係であった。The yield of 3-hydroxy-4,5-dimethoxybenzaldehyde was 79%.
比較例 １
３．４−ジヒドロキシ−５−メトキシベンズアルデヒド
８．４ ｊｊ （５０ｍｍｏｌ）をＩＮ力性ソーダ水溶
液５０ｍ１に溶解し、撹拌しながらジメチル硫酸６、７
ｇ（５５ｍｍｏｌ）を滴下した。Comparative Example 1 8.4 jj (50 mmol) of 3.4-dihydroxy-5-methoxybenzaldehyde was dissolved in 50 ml of IN aqueous sodium hydroxide solution, and 6,7 ml of dimethyl sulfate was added while stirring.
g (55 mmol) was added dropwise.
室温で２４時間反応後、希塩酸で微酸性にしてエーテル
で抽出し、抽出液をガスクロマトグラフ分析した。After reacting at room temperature for 24 hours, the mixture was made slightly acidic with dilute hydrochloric acid, extracted with ether, and the extract was analyzed by gas chromatography.
３−ヒドロキシ−４，５−ジメトキシベンズアルデヒド
の収率は４０％、３，４．５−トリメトキシベンズアル
デヒドの収率は１０％、シリンガアルデヒドの収率は８
係であった。The yield of 3-hydroxy-4,5-dimethoxybenzaldehyde is 40%, the yield of 3,4.5-trimethoxybenzaldehyde is 10%, and the yield of syringaldehyde is 8%.
He was in charge.
比較例 ２
アルカリ剤として、ＩＮ力性ソーダ水溶液の替わりにＩ
Ｎ力性カリ水溶液を用いた以外は比較例１と同様に反応
させた。Comparative Example 2 As an alkaline agent, I
The reaction was carried out in the same manner as in Comparative Example 1 except that an N-potassium aqueous solution was used.
反応生成物をガスクロマトグラフ分析した。The reaction product was analyzed by gas chromatography.
３−ヒドロキシ−４，５−ジメトキシベンズアルデヒド
の収率は４０係、３．４．５−トリメトキシベンズアル
デヒドの収率は１７ｆｏ、シリンガアルデヒドの収率は
１３係であった。The yield of 3-hydroxy-4,5-dimethoxybenzaldehyde was 40%, the yield of 3.4.5-trimethoxybenzaldehyde was 17fo, and the yield of syringaldehyde was 13%.
実施例 ４
３．４−ジヒドロキシベンズアルデヒド６．９ｇ（５０
ｍｍｏｌ）、ジメチル硫酸６．５９ （５５ｍｍｏｌ）
及び炭酸ナトリウム６．０ ｇ（５７ｍｍｏｌ）をアセ
トン８ＯｒｒＬｌ中に加え、４時間、還流温度で反応さ
せた。Example 4 6.9 g (50
mmol), dimethyl sulfate 6.59 (55 mmol)
and 6.0 g (57 mmol) of sodium carbonate were added to 8 OrrLl of acetone and reacted for 4 hours at reflux temperature.
反応生成物をガスクロマトグラフ分析した。３−ヒドロ
キシ−４−メトキシベンズアルデヒドの収率は８７％、
３−メトキシル４−ヒドロキシベンズアルデヒドの収率
は５％、ベラトルムアルデヒドの収率は３係であった。The reaction product was analyzed by gas chromatography. The yield of 3-hydroxy-4-methoxybenzaldehyde was 87%.
The yield of 3-methoxyl 4-hydroxybenzaldehyde was 5%, and the yield of veratrumaldehyde was 3%.
実施例 ５
溶媒をアセトンからジオキサンに替えた以外は実施例４
と同様に１００℃で２時間反応させた。Example 5 Example 4 except that the solvent was changed from acetone to dioxane
Similarly, the reaction was carried out at 100°C for 2 hours.
反応生成物をガスクロマトグラフ分析した。The reaction product was analyzed by gas chromatography.
３−ヒドロキシ−４−メトキシベンズアルデヒドの収率
は８５係であった。The yield of 3-hydroxy-4-methoxybenzaldehyde was 85%.
実施例 ６
溶媒をアセトンからジメチルスルホキシドに替えた以外
は実施例４と同様に１００℃で２時間反応させた。Example 6 A reaction was carried out at 100° C. for 2 hours in the same manner as in Example 4 except that the solvent was changed from acetone to dimethyl sulfoxide.
反応生成物をガスクロマトグラフ分析した。The reaction product was analyzed by gas chromatography.
３−ヒドロキシ−４−メトキシベンズアルデヒドの収率
は９０係であった。The yield of 3-hydroxy-4-methoxybenzaldehyde was 90%.
Claims (1)
）で表わされる３、４−ジヒドロキシベンズアルデヒド
化合物１モルに対してジメチル硫酸を１〜１．２モルの
割合で加え、炭酸すｔ−ＩＪウムの存在下に非プロトン
性極性溶媒中で反応させることを特徴とする、一般式； （ただし、式中のＲは前記と同じ意味を有する）で表わ
される３−ヒドロキシ−４−メトキシベンズアルデヒド
化合物の製法。[Claims] 1. 1 to 1.2 mol of dimethyl sulfuric acid per 1 mol of the 3,4-dihydroxybenzaldehyde compound represented by the general formula; (R in the formula represents a hydrogen atom or an alkoxy group) (However, R in the formula has the same meaning as above). A method for producing a 3-hydroxy-4-methoxybenzaldehyde compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6949479A JPS5822136B2 (en) | 1979-06-05 | 1979-06-05 | Method for producing 3-hydroxy-4-methoxybenzaldehyde compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6949479A JPS5822136B2 (en) | 1979-06-05 | 1979-06-05 | Method for producing 3-hydroxy-4-methoxybenzaldehyde compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55162731A JPS55162731A (en) | 1980-12-18 |
| JPS5822136B2 true JPS5822136B2 (en) | 1983-05-06 |
Family
ID=13404314
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6949479A Expired JPS5822136B2 (en) | 1979-06-05 | 1979-06-05 | Method for producing 3-hydroxy-4-methoxybenzaldehyde compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5822136B2 (en) |
-
1979
- 1979-06-05 JP JP6949479A patent/JPS5822136B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55162731A (en) | 1980-12-18 |
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