JPH0625156B2 - Phenyl pyrimidine derivative - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a liquid crystal compound used in a liquid crystal display device, particularly,
It is used as an important intermediate compound for synthesizing liquid crystal compounds having chiral smectic performance.

[Conventional technology]

Conventionally, as a liquid crystal compound, (In the formula, X represents H, Cl and CN, Y represents Cl and C ₂ H ₅ ,
* Indicates an asymmetric carbon atom. ) Compound, [Ferroelectrics, 24 (1980)
309, Mol. Cryst. Liq. Cryst. ,
Letter 82 (1982) 61] See also [In the above three compounds, n is 9 or 10. ] B. I. It is manufactured by Ostrovskii et al.

However, these known liquid crystal compounds do not exhibit a chiral smectic phase in a wide temperature range and have a problem in stability.

[Problems to be Solved by the Present Invention]

An object of the present invention is to solve various problems in the prior art, that is, various liquid crystals having excellent stability, exhibiting a chiral smectic phase in a wide temperature range, and having excellent miscibility with other liquid crystal compounds. The formula [I] that is essential for making a compound [Wherein A is the longest chain end carbon atoms 3 Ke th represents an alkyl group of C ₆ -C ₁₅ are asymmetric carbon atoms, bonded to the pyrimidine ring without or via an oxygen atom Another object of the present invention is to provide a phenylpyrimidine derivative represented by

[Means for solving problems]

The target compound of the present invention is synthesized by the following chemical reaction formula.

[Synthesis Method 1] [Synthesis Method 2] [In the reaction formula, A is the same as described above, R ₁ is hydrogen or a group that can be used as a protecting group for phenol such as benzyl, phenethyl and benzoyl, and X is a halogen atom. R represents a lower alkyl group, or R may be the same as A in view of the reaction mechanism between the compound of the formula [II] and Vilsmeier reagent. The compound represented by the formula [II] or an aldehyde compound derived therefrom is treated with haloalkane such as methylene chloride and chloroform, in a solvent such as N, N-dimethylformamide, thionyl chloride, phosphorus oxychloride, phosgene and trichloromethylchloro chloride. The acrolein derivative represented by the formula [III] is obtained by reacting a formate or the like with a Vilsmeier reagent obtained by the reaction of N, N-dimethylformamide, dimethylacetamide or the like N, N-dialkylacylamide. obtain. Then, the benzamidine derivative represented by the formula [IV] or a salt thereof is treated with a metal alcoholate catalyst (for example, methanol, ethanol, propanol, isopropanol), benzene, toluene, N, N-dimethylformamide or the like in a solvent such as , Sodium methylate, sodium ethylate, potassium t-butyrate) or an alkali metal (for example, sodium, potassium) to give the compound of the present invention represented by the formula [I]. Formula (I
When R _{1 of the} compound represented by V] is a group which can be used as a protecting group for phenol, after the reaction with the compound of the formula [III], the obtained compound is subjected to a usual reaction such as catalytic reduction or hydrolysis. By appropriately selecting and using, the protecting group can be eliminated and the compound of the present invention can be introduced.

The compound of the present invention can also be prepared by the method shown in [Synthesis Method 2]. That is, a compound represented by the formula [V] and a compound represented by the formula [IV] are mixed with alcohols such as methanol and ethanol, benzene, toluene and DMS.
By reacting in the presence of a metal alcoholate or an alkali metal in a solvent such as O or DMF that does not participate in the reaction, a compound represented by the formula [VI] is obtained. This reaction is preferably carried out under reflux. Then, the compound represented by the formula [VI], in the presence or absence of a solvent as appropriate, phosphorus oxyhalide (for example, phosphorus oxychloride, phosphorus oxybromide),
The dihalogenopyrimidine derivative represented by the formula [VII] is obtained by reacting with a halogenating agent such as phosphorus tri- or penta-halogenated in the presence of a catalyst under reflux. Examples of the catalyst used here include basic catalysts such as N, N-diethylaniline and pyridine, but N, N-diethylaniline is preferable.

Then, the compound represented by the formula [VII] undergoes elimination of the protecting group and dehalogenation by catalytic reduction or the like to give the compound of the formula [I]
The target compound represented by is obtained. When R _{1 of the} compound represented by the formula [I] is hydrogen or a protecting group other than benzyl, dehalogenation is carried out by catalytic reduction, and then a reaction such as acid or alkali hydrolysis is carried out, The target compound is obtained.

Further, in the object compound of the present invention, when A has an asymmetric carbon atom, there exists a pair of optical antipodes, which are all included in the object compound of the present invention. In the compound represented by the formula [II] or the formula [V] used as a raw material, the optical properties of the target compound are uniquely determined depending on which of the optical antipodes is used.

Hereinafter, examples will be described in order to specifically describe the present invention.

Reference Example 1 Synthesis of 2- (n-octyloxy) acetaldehyde diethyl acetal Dissolve 22 g of n-octyl alcohol in 10 m of dry toluene in 8.92 g (0.186 mol) of 50% sodium hydride, and gradually add dropwise. The mixture is then refluxed until hydrogen gas evolution ceases (about 30 minutes). The internal temperature was lowered to 80 ° C., 34.3 g (0.69 mol) of bromoacetaldehyde diethyl acetal (97%) was dissolved in 40 m of dried N, N-dimethylformamide, and the solution was added in about 30 minutes. After the addition of the whole amount is completed, the content is adjusted to 80-90.
After stirring and reacting at 25 ° C. for 25 hours, the content is distilled off under reduced pressure to about half the volume. Water and ether are added to the residue and the product is extracted with ether. The ether layer was washed with brine, dried over magnesium sulfate, and the oily residue obtained by distilling off the solvent was distilled under reduced pressure to distill the target compound, 2- (n-octyloxy) acetaldehyde diethyl acetal 2
1 g was obtained.

b. p. 119-123 ° C / 3-4mmHg ¹ H-NMR (60 MHz. CCl ₄ ) δ (p.p.m.): 0.6 to 1.70 (m.21H) 3.10 to 3.70 (m.8H) 4.45 (t.1H) Reference Example 2 β-Dimethylmino-α Synthesis of-(n-octyloxy) acrolein; dried N in 300 m4 diameter flask,
24.36 g of N-dimethylformamide and 50 m of dried ethylene dichloride are taken, the content is cooled to -10 ° C, and 27.4 g of phosphorus oxychloride is dissolved in 20 m of dried ethylene dichloride and added dropwise. Stir for 30 minutes at an internal temperature of 0 to 3 ° C,
At the same temperature, 20 g of 2- (n-octyloxy) acetaldehyde diethyl acetal was dried with 30 m of ethylene dichloride.
Dissolve in and add at room temperature for 30 minutes, then warm to 70
After raising the temperature to 50 ° C. and stirring at this temperature for 50 minutes, the reaction mixture was cooled, poured into ice water, made alkaline with 70 m of a saturated aqueous solution of potassium carbonate, concentrated under reduced pressure, the solvent was distilled off, and the two layers were separated. The test solution was heated at 90 ° C. for 30 minutes, and then the product was extracted with a mixed solvent of benzene-ethanol (2: 1) to obtain 27 g of an oily residue. This oil was vacuum distilled to give β-dimethylamino-α- (n-octyloxy).
4.74 g of acrolein was obtained.

b. p. 140-160 [deg.] C./5 mmHg IR [nu] maxcm < ^-1 >: 2720.1605.1395.
1275.1180.1115.785. ¹ H-NMR (60 MHz. CDCl ₃ ) δ (ppm): 0.6-1.90 (m.15H) 3.08 (s.6H) 3.78 (t.2H) 6.06 (s.1H) 8.51 (s.1H) Reference Example 3 Synthesis of 2- (4-hydroxyphenyl) -5- (n-octyloxy) pyrimidine: 4-hydroxybenzamidine hydrochloride 4.3 g, β-dimethylamino-α- (n-octyloxy) acrolein in a 100 m round-bottomed flask. Take 5.7 g, dissolve in 40 m of ethanol, add 19.3 g of 28% sodium methylate methanol solution, reflux for 8 hours, pour into ice water, acidify with dilute sulfuric acid water, and add ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over magnesium sulfate, and evaporated to give 7.1 g of an oily substance.

After treatment with n-hexane-ethanol for crystallization and purification, 2.79 g of 2- (4-hydroxyphenyl) -5-
(N-octyloxy) pyrimidine was obtained.

¹ H-NMR (60 MHz. CDCl ₃ ) δ (p.p.m.): 0.6 to 2.2 (m.17H) 4.02 (t.2H) 6.85 (d.2H) 8.16 (d.2H) 8.43 (s. 2H) Reference Example 4 Synthesis of 2- (n-hexyloxy) acetaldehyde diethyl acetal A hexyl alcohol and bromo acetal were used and synthesized in the same manner as in Example 1.

Yield 50% b. p. 85-95 ° C./5 mmHg IRνmaxcm ⁻¹ : 1460.1380.1120.
1070 ¹ H-NMR (60 MHz.CDCl ₃ ) δ (ppm) 0.60 to 1.80 (m.17H) 3.20 to 4.00 (m.8H) 4.59 (t.1H) Reference Example 5 β-Dimethylamino-α- (n- Synthesis of Hexyloxy) acrolein: Prepared in a similar manner to Example 2 using 2- (n-hexyloxy) acetaldehyde diethyl acetal and Vilsmeier reagent obtained from dimethylformamide and trichloromethylchloroformate. Ivy.

Yield 25% b. p. 131-145 [deg.] C./3 mmHg IR [nu] maxcm < ^-1 >: 2745.1610.1410.
1280.1185.1120.790 ¹ H-NMR (60 MHz.CDCl ₃ ) δ (ppm): 0.67 to 2.00 (m.11H) 3.10 (s.6H) 3.82 (t.2H) 6.12 (s.1H) 8.53 ( s.1H) Reference Example 6 Synthesis of 2- (4-hydroxyphenyl) -5- (n-hexyloxy) pyrimidine.

It was synthesized in the same manner as in Example 3 using β-dimethylamino-α- (n-hexyloxy) acrolein and 4-hydroxybenzamidine hydrochloride. Yield 60% IR? Maxcm- ¹ : 3350 to 3050.1610.
1595.1430.1280.1245 ¹ H-NMR (60 MHz.CDCl ₃ ) δ (ppm): 0.6 to 2.10 (m.11H) 4.00 (t.2H) 6.80 (d.2H) 8.12 (d.2H) 8.40 ( s.2H) Reference Example 7 Synthesis of (n-undecyloxy) acetaldehyde diethyl acetal 11.73 g of metallic sodium in a 500 m four-necked flask,
200 m of dry tetrahydrofuran, 50 m of dry N, N-dimethylformamide, and 80 g of n-undecyl alcohol were added to prepare a sodium salt of n-undecyl alcohol. Then, 91.5 g of bromoacetaldehyde diethyl acetal was added dropwise at room temperature over 1 hour.
Furthermore, after reacting for 60 minutes at room temperature, the reaction was carried out under reflux for 12.5 hours. After the reaction was completed, it was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and saturated saline and then dried, and ethyl acetate was distilled off.

The oily substance obtained was distilled under reduced pressure to obtain a temperature of 134 to 138 ° C / 3 mm.
55.3 g of Hg fraction was obtained.

¹ H-NMR (60 MHz.CDCl ₃ ) δ (ppm): 0.5 to 1.9 (m.27H) 3.20 to 3.95 (m.8H) 4.65 (t.1H) Reference Example 8 β-Dimethylamino-α- (n- Synthesis of undecyloxy) acrolein 26 g of dried N, N-dimethylformamide was placed in a 500 m four-necked flask and dried of ethylene dichloride 4
Dissolve in 3m, dry ice-acetone bath -1
29.91 g of trichloromethyl chloroformate dissolved in 22 m of dry ethylene dichloride, keeping at 0 ° C or below
Was added dropwise over 40 minutes.

After reacting for 1 hour, 25 g of 2- (n-undecyloxy) acetaldehyde diethyl acetal dissolved in 30 m of dry ethylene dichloride at -10 ° C to 5 ° C was used.
Dropped in minutes. After dropping, the temperature was returned to room temperature over 1 hour, and further raised to 67 ° C over 2 hours, and at 67 ° C,
Reacted for 1 hour. After completion of the reaction, the reaction mixture was cooled, 50m saturated aqueous potassium carbonate solution was added to make the mixture alkaline, the solvent was distilled off under reduced pressure, and the residue was refluxed at 90 to 100 ° C for 20 minutes, then cooled and cooled to benzene-ethanol (2: The reaction product was extracted in 1). The extract was dried over sodium carbonate and the solvent was evaporated to give an oil. This oily substance was distilled under reduced pressure to obtain β-
5.5 g of dimethylamino-α- (n-undecyloxy) acrolein was obtained.

b. p. 186 ~ 196 ℃ / 3mmHg ¹ H-NMR (60 MHz.CDCl ₃ ) δppm: 0.7 to 1.9 (m.21H) 3.11 (s.6H) 3.83 (t.2H) 6.15 (s.1H) 8.62 (s.1H) Reference Example 9 2- ( Synthesis of 4-hydroxyphenyl) -5- (n-undecyloxy) pyrimidine In a 50 m round-bottomed flask, 1.92 g of 4-hydroxybenzamidine hydrochloride and 3 g of α-undecyloxy-β-dimethylaminoacrolein were placed and dried. Ethanol 3
After dissolving in 0 m, 8.5 g of 28% sodium methylate methanol solution was added and reacted under reflux for 8 hours.
After that, the reaction solution was poured into ice water and acidified with hydrochloric acid, and the reaction product was extracted with ethyl acetate. The organic layer was washed with water and saturated saline, dried over magnesium sulfate, the solvent was distilled off, and the residue was purified by silica gel column chromatography to give 2- (4-hydroxyphenyl) -5. −
2.53 g of (n-undecyloxy) pyrimidine was obtained.

IRνmaxcm ^-1 : 161.1602.1550.
1438 ¹ H-NMR (60 MHz.CDCl ₃ ) δ (ppm): 0.7 to 2.2 (m.21H) 4.12 (t.2H) 6.90 (d.2H) 8.20 (d.2H) 8.47 (s.2H) Example 1 1) Synthesis of 1-acetyloxy-7-methylnonane: 2.42 g of metallic magnesium in a 200 m 4 diameter flask.
(0.01 gram atom), dry tetrahydrofuran 50
m, a small amount of iodine was taken, 17.86 g (0.01 mol) of (S) -4-methylhexyl bromide dissolved in 50 m of dry tetrahydrofuran was added dropwise, and the mixture was further refluxed for 2 hours to prepare a Grignard reagent. did. Cuprous iodide 2.15 in another 500 m 4-diameter flask.
g was suspended in 40 m of dry tetrahydrofuran,
It was cooled to -70 ° C with dry ice-acetone, and the Grignard reagent prepared above was required for 15 minutes while stirring.
The solution was added dropwise while maintaining the internal temperature of -65 ° C to -70 ° C. After stirring at the same temperature for 30 minutes, 18.2 g (0.08 mol) of 1-acetyloxy-3-iodopropane was dried in tetrahydrofuran 2
Dissolve in 5m, take 10 minutes, -65 ℃ ~ -7
After dropping at 0 ° C., the mixture was further stirred at the same temperature for 15 minutes, the cooling bath was changed to an ice water bath, the temperature was raised to room temperature, and then the mixture was refluxed for 6 hours. The reaction solution was poured into ice-ammonium chloride to decompose, ether was added, and insoluble materials were separated,
The ether layer was separated, washed with brine and dried over magnesium sulfate.

The solvent was distilled off to obtain 18.62 g of an oily substance. This oily substance was subjected to the next reaction without purification.

IR? Maxcm- ¹ : 174.1460.1365.
1235.1040 2) (S) -7-Methylnonan-1-ol: 1-Acetyloxy-7-methylnonane crude oil 18.6
Dissolve 2g in 105m methanol and 15m water,
19.5 g of sodium hydroxide was added, and the mixture was refluxed for 2 hours, acidified with dilute hydrochloric acid, extracted with ether, washed with brine and dried over magnesium sulfate, and the solvent was evaporated to give an oil.
11.33 g of (S) -7-methylnonan-1-ol was obtained.

This product was subjected to the next reaction without purification.

IR? Maxcm- ¹ : 3350.1460.1375.
1055 3) Synthesis of (S) -1-bromo-7-methylnonane: 11.33 g of crude (S) -7-methylnonane-1-ol oil obtained in 2) was added to 47% hydrobromic acid aqueous solution 24.6. g and 7.73 g of concentrated sulfuric acid and refluxed for 6 hours,
It was poured into ice, extracted with ether, washed with brine, saturated aqueous sodium hydrogen carbonate solution, and brine, washed with calcium chloride, and the ether was distilled off to obtain 14.0 g of an oily substance. The oil was vacuum distilled to give 12.14 g of (S) -1-bromo-7-methylnonane.

b. p. 116-121 ° C / 20 mmHg IRνmaxcm ^-1 : 2960.2930.2860.
1460.1380.1255. Example 2 Synthesis of (S) -β-dimethylamino-α- (6-methyloctyl) acrolein 1) Synthesis of (S) -8-methyldecylaldehyde diethyl acetal In a 100 m2 diameter flask, 1.33 g of metallic magnesium was added.
(0.055 gram atom), dried ether 25 m, catalytic amount of iodine was added thereto, and (S) -7-methylnonyl bromide 12.14 g (0.055 mol) was dried ether 40 m.
After being dissolved in the solution, the solution is added dropwise and then refluxed for 2 hours to prepare a Grignard reagent.

Then, in another 200 m 4-diameter flask, 8.95 g (0.06 mol) of ethyl orthoformate is dissolved in 10 m of dried ether, and the Grignard reagent prepared above is added dropwise with stirring. After dropping the whole amount, the mixture was reacted under reflux for 24 hours and then poured into ice water-ammonium chloride to decompose. The product was extracted with ether, washed with brine, dried over magnesium sulfate, and the ether was distilled off to obtain 11.0 g of an oily substance.

This oily substance was distilled under vacuum to obtain 7.6 g of (S) -8-methyldecylaldehyde diethyl acetal.

b. p. 126-131 ° C / 6 mmHg IRvmaxcm ^-1 : 2950.2930.2850.
1460.1375.1125.1060 ¹ H-NMR (60 MHz.CCl ₄ ) δ (ppm): 0.5 to 2.20 (m.21H) 2.95 to 3.80 (m.4H) 3.40 (t.1H) 2) (S)- Synthesis of β-dimethylamino-α- (6-methyloctyl) acrolein Dry N, N-dimethylformamide 10.27 g, dry ethylene dichloride 40 m in a 200 m 4-diameter flask.
Was cooled to -10 ° C to -15 ° C, and a solution of 12.82 g of trichloromethyl chloroformate and 15 m of dried ethylene dichloride was added dropwise to the solution to prepare Vilsmeier reagent, to which 8-methyldecylaldehyde was added. A solution obtained by dissolving 7.6 g of diethyl acetal in 15 m of dried ethylene dichloride was added dropwise.

After stirring for 20 minutes at room temperature, it took 1 hour to raise the temperature to 70 ° C,
The reaction is further performed at the same temperature for 1 hour. The reaction solution was cooled and made alkaline with a saturated aqueous solution of potassium carbonate, the solvent was distilled off, and the residue was heated at 90 to 100 ° C. for 2 hours. Cooled, extracted with a mixed solvent of benzene-ethanol (2: 1), dried over sodium carbonate and evaporated to give a crude oily substance.
8.72 g was obtained.

This oily substance was distilled under vacuum to obtain 5.1 g of (S) -β-dimethylamino-α- (6-methyloctyl) acrolein.

b. p. 180-193 ° C / 6 mmHg IRνmaxcm _-1 : 2720.1595.1395.
1380.1125 ¹ H-NMR (60 MHz.CCl ₄ ) δ (ppm): 0.5 to 1.60 (m.17H) 2.32 (t.2H) 3.17 (s.6H) 6.44 (s.1H) 8.85 (s.1H) Example 3 Synthesis of (S) -2- (4-hydroxyphenyl) -5- (6-methyloctyl) pyrimidine: 1.91 g of 4-hydroxybenzamidine hydrochloride, (S) -β-dimethyl in a 50 m round-bottomed flask. Amino-α- (6-
2.5 g of methyloctyl) acrolein was added, 8.98 g of a dry ethanol solution was added, and the mixture was reacted under reflux for 8 hours. After the reaction was completed, it was poured into ice water, acidified with hydrochloric acid, and the reaction product was extracted with ethyl acetate.

The ethyl acetate layer was washed with water and saturated saline and then dried, and the organic solvent was evaporated under reduced pressure. The obtained oily substance was purified by silica gel chromatography to obtain 2.5 g of (S) -2- (4-hydroxyphenyl) -5- (6-methyloctyl) pyrimidine.

¹ H-NMR (60 MHz.CDCl ₃ ) δ (ppm): 0.6 to 2.0 (m.17H) 2.62 (t.2H) 8.25 (d.2H) 8.87 (d.2H) 8.60 (s.2H) Example 4 (S) -2- (6-Methyl-octyloxy) acetaldehyde diethyl acetal In a 200 m4 diameter flask, 2.72 g of sodium metal
(0.118 gram atom) put and dried toluene 10m
Was added and the contents were stirred and refluxed with (S) -6-methyl-
Octane-1-ol (This compound was obtained by performing the malonate synthesis method twice from (S) -amyl alcohol.) 5.53 g (0.108 mol) was dissolved in 20 m of dry toluene and added dropwise. After the contents were refluxed for 3 to 4 hours, 22 g of bromoacetaldehyde diethyl acetal (0.11
16 mol) to dry N, N-dimethylformamide 3
It was dissolved in 5 m and added, and the reaction was carried out at 80 to 90 ° C. for 24 hours. Ice water was added to the reaction solution, the product was extracted with ether, the ether layer was washed with saturated brine and dried over magnesium sulfate, and then the ether was distilled off to obtain 29.58 g of an oily substance. The oil was vacuum distilled to give (S) -2- (6-
17.16 g of methyl-octyloxy) acetaldehyde diethyl acetal were obtained.

b. p. 130-133 ℃ / 5mmHg ¹ H-NMR (60 MHz.CDCl ₃ ) δ (ppm): 0.5 to 1.70 (m.23H) 3.10 to 3.75 (m.8H) 4.42 (t.1H) Example 5 (S) -β-dimethylamino-α Synthesis of-(6-methyloctyloxy) acrolein: In a 200 m 4-diameter flask, 12 g (0.1642 mol) of dried N, N-dimethylformamide was taken and dissolved in 40 m of dried ethylene dichloride, and the content was cooled at -10 ° C. To do.

Trichloromethyl chloroformate 15
g (0.06993 mol) of dried ethylene dichloride 15m
And is added dropwise while maintaining the internal temperature at -10 ° C. After the dropping, the mixture is stirred for 15 minutes to raise the internal temperature to 0 ° C.

In addition to this, (S) -2- (6-methyl-octyloxy)
Acetaldehyde diethyl acetal 10 g (0.03995
Mol) in 15 m of dry ethylene dichloride,
Add 7-10 minutes. After stirring the reaction mixture at room temperature for 15 minutes, it took 1 hour to raise the internal temperature to 70 ° C.,
Stirring reaction is further performed at the same temperature for 1 hour. Then, the reaction solution was cooled, 50m saturated aqueous potassium carbonate solution was added, and the mixture was rendered alkaline without concentration and the solvent was distilled off.
The residue separated into layers was refluxed at 90 ° C to 100 ° C for 20 minutes, cooled, extracted with benzene-ethanol (2: 1), dried over sodium carbonate, and the solvent was distilled off to give an oily residue. 10 g are obtained.

This was vacuum distilled to give (S) -β-dimethylamino-
α- (6-Methyloctyloxy) acrolein 2.53g
Get.

b. p. 180-190 ℃ / 5mmHg ¹ H-NMR (60 MHz. CCl ₄ ) δ (ppm): 0.6 to 1.90 (m.17H) 3.06 (s.6H) 3.75 (t.2H) 5.97 (s.1H) 8.43 (s.1H) Example 6 Synthesis of (S) -2- (4-hydroxyphenyl) -5- (6-methyloctyloxy) pyrimidine 4-hydroxybenzamidine hydrochloride 2.85 g, (S) -α
Ethyl alcohol 3 obtained by drying 4.0 g of-(6-methyloctyloxy) -β- (dimylamino) acrolein
It was dissolved in 0 m, 12.78 g of 28% sodium methylate-methanol solution was added, and the reaction was carried out for 8 hours under reflux with stirring. The reaction solution was poured into ice water, acidified with dilute hydrochloric acid aqueous solution, the product was extracted with ethyl acetate, the organic layer was washed with water and saturated brine, dried over magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography to obtain (S) -2- (4-hydroxyphenyl) -5- (6-methyloctyloxy) pyrimidine (3.12 g).

IRvmaxcm- ¹ : 3350 to 3050.1610.
1595.1280.1245.1175 ¹ H-NMR (60 MHz.CDCl ₃ ) δ (ppm): 0.6 to 2.10 (m.17H) 4.04 (t.2H) 8.30 (d.2H) 6.90 (d.2H) 8.45 ( s.2H) The compound obtained by the present invention is disclosed in Japanese Patent Application No. 60-56652 (Japanese Patent Application Laid-Open No. 61-2) filed by the applicant of the present invention.
No. 15372), it is used as a raw material for synthesizing a ferroelectric chiral smectic liquid crystal compound.

Claims (1)

[Claims] 1. A formula [Wherein A represents a C _{6 to} C ₁₅ alkyl group in which the third carbon atom from the end of the longest chain is an asymmetric carbon atom, and is bonded to the pyrimidine ring through an oxygen atom or not] Phenylpyrimidine derivative