JPH02204469A - １，８―ビス（２―ヒドロキシエチル）ナフタレン、その誘導体、およびこれらの製造方法 - Google Patents
１，８―ビス（２―ヒドロキシエチル）ナフタレン、その誘導体、およびこれらの製造方法Info
- Publication number
- JPH02204469A JPH02204469A JP2440789A JP2440789A JPH02204469A JP H02204469 A JPH02204469 A JP H02204469A JP 2440789 A JP2440789 A JP 2440789A JP 2440789 A JP2440789 A JP 2440789A JP H02204469 A JPH02204469 A JP H02204469A
- Authority
- JP
- Japan
- Prior art keywords
- bis
- naphthalene
- hydroxyethyl
- formula
- tables
- 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.)
- Granted
Links
- NTAAJJCJYRBUBY-UHFFFAOYSA-N 2-[8-(2-hydroxyethyl)naphthalen-1-yl]ethanol Chemical compound C1=CC(CCO)=C2C(CCO)=CC=CC2=C1 NTAAJJCJYRBUBY-UHFFFAOYSA-N 0.000 title claims abstract description 18
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims abstract description 19
- FTUDIUREWUBVKL-UHFFFAOYSA-N 1,8-bis(ethenyl)naphthalene Chemical compound C1=CC(C=C)=C2C(C=C)=CC=CC2=C1 FTUDIUREWUBVKL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 7
- 125000002252 acyl group Chemical group 0.000 claims abstract description 5
- VHAXQSFPTJUMLT-UHFFFAOYSA-N bis(3-methylbutan-2-yl)boron Chemical compound CC(C)C(C)[B]C(C)C(C)C VHAXQSFPTJUMLT-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 4
- DJPYSBJGYBNFPQ-UHFFFAOYSA-N 2-[1-(2-hydroxyethyl)naphthalen-2-yl]ethanol Chemical class C1=CC=CC2=C(CCO)C(CCO)=CC=C21 DJPYSBJGYBNFPQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 13
- 239000002994 raw material Substances 0.000 abstract description 3
- 239000000178 monomer Substances 0.000 abstract description 2
- 229920000728 polyester Polymers 0.000 abstract description 2
- 229920000570 polyether Polymers 0.000 abstract description 2
- 239000004094 surface-active agent Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- ONHYGEBPSXWFBW-UHFFFAOYSA-N [B].C(=C)C1=CC=CC2=CC=CC(=C12)C=C Chemical compound [B].C(=C)C1=CC=CC2=CC=CC(=C12)C=C ONHYGEBPSXWFBW-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
- RXWNCMHRJCOWDK-UHFFFAOYSA-N 2-naphthalen-1-ylethanol Chemical compound C1=CC=C2C(CCO)=CC=CC2=C1 RXWNCMHRJCOWDK-UHFFFAOYSA-N 0.000 description 1
- 125000004917 3-methyl-2-butyl group Chemical group CC(C(C)*)C 0.000 description 1
- SFLRIYPIOABSJV-UHFFFAOYSA-N B([O-])([O-])[O-].B([O-])([O-])[O-].B([O-])([O-])[O-].[B+3].[B+3].[B+3] Chemical compound B([O-])([O-])[O-].B([O-])([O-])[O-].B([O-])([O-])[O-].[B+3].[B+3].[B+3] SFLRIYPIOABSJV-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- DINZUYYYXDLSJE-UHFFFAOYSA-N [8-(hydroxymethyl)naphthalen-1-yl]methanol Chemical compound C1=CC(CO)=C2C(CO)=CC=CC2=C1 DINZUYYYXDLSJE-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- -1 and then Chemical compound 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical compound [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000006197 hydroboration reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2440789A JPH02204469A (ja) | 1989-02-02 | 1989-02-02 | １，８―ビス（２―ヒドロキシエチル）ナフタレン、その誘導体、およびこれらの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2440789A JPH02204469A (ja) | 1989-02-02 | 1989-02-02 | １，８―ビス（２―ヒドロキシエチル）ナフタレン、その誘導体、およびこれらの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02204469A true JPH02204469A (ja) | 1990-08-14 |
| JPH0460591B2 JPH0460591B2 (it) | 1992-09-28 |
Family
ID=12137317
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2440789A Granted JPH02204469A (ja) | 1989-02-02 | 1989-02-02 | １，８―ビス（２―ヒドロキシエチル）ナフタレン、その誘導体、およびこれらの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02204469A (it) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018232552A1 (zh) * | 2017-06-19 | 2018-12-27 | 陈德如 | 一种双(3-甲基-2-丁基)硼烷的制备方法 |
-
1989
- 1989-02-02 JP JP2440789A patent/JPH02204469A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018232552A1 (zh) * | 2017-06-19 | 2018-12-27 | 陈德如 | 一种双(3-甲基-2-丁基)硼烷的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0460591B2 (it) | 1992-09-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |