HU183288B - Process for preparing new 4-/1-hydroxy-1-methyl-ethyl/-3-cyclohexen-1-one-ketals - Google Patents
Process for preparing new 4-/1-hydroxy-1-methyl-ethyl/-3-cyclohexen-1-one-ketals Download PDFInfo
- Publication number
- HU183288B HU183288B HU81128A HU12877A HU183288B HU 183288 B HU183288 B HU 183288B HU 81128 A HU81128 A HU 81128A HU 12877 A HU12877 A HU 12877A HU 183288 B HU183288 B HU 183288B
- Authority
- HU
- Hungary
- Prior art keywords
- hydroxy
- cyclohexen
- methyl
- ketals
- ethyl
- Prior art date
Links
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 8
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- -1 cyclohexenone carboxylate Chemical class 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- RCZLCLVMJHKZAJ-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)cyclohex-3-en-1-one Chemical compound CC(C)(O)C1=CCC(=O)CC1 RCZLCLVMJHKZAJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- MPXHGMFNVXPWFF-UHFFFAOYSA-N methyl 4-oxocyclohexene-1-carboxylate Chemical compound COC(=O)C1=CCC(=O)CC1 MPXHGMFNVXPWFF-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003509 tertiary alcohols Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XBUBZYADIWHLQQ-UHFFFAOYSA-N 2-(2-hydroxypropan-2-yl)cyclohexan-1-one Chemical compound CC(C)(O)C1CCCCC1=O XBUBZYADIWHLQQ-UHFFFAOYSA-N 0.000 description 1
- VNAWKNVDKFZFSU-UHFFFAOYSA-N 2-ethyl-2-methylpropane-1,3-diol Chemical compound CCC(C)(CO)CO VNAWKNVDKFZFSU-UHFFFAOYSA-N 0.000 description 1
- YEKAIIDBUIVJGJ-UHFFFAOYSA-N C=C.COC(=O)C1=CCC(CC1)=O Chemical group C=C.COC(=O)C1=CCC(CC1)=O YEKAIIDBUIVJGJ-UHFFFAOYSA-N 0.000 description 1
- SKRLDOPLNGDYAD-UHFFFAOYSA-N CC(CO)(CO)C.COC(=O)C1=CCC(CC1)=O Chemical compound CC(CO)(CO)C.COC(=O)C1=CCC(CC1)=O SKRLDOPLNGDYAD-UHFFFAOYSA-N 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- SHALBPKEGDBVKK-VOTSOKGWSA-N danishefsky's diene Chemical compound CO\C=C\C(=C)O[Si](C)(C)C SHALBPKEGDBVKK-VOTSOKGWSA-N 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- AFJTZYYVUBIMNH-UHFFFAOYSA-N methyl 2-methoxy-4-trimethylsilyloxycyclohex-3-ene-1-carboxylate Chemical compound COC1C=C(O[Si](C)(C)C)CCC1C(=O)OC AFJTZYYVUBIMNH-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pyrane Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/702,804 US4054581A (en) | 1976-07-06 | 1976-07-06 | Preparation of cis-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-ones and intermediates therefor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU183288B true HU183288B (en) | 1984-04-28 |
Family
ID=24822669
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU81128A HU183288B (en) | 1976-07-06 | 1977-07-05 | Process for preparing new 4-/1-hydroxy-1-methyl-ethyl/-3-cyclohexen-1-one-ketals |
| HU77EI751A HU177307B (en) | 1976-07-06 | 1977-07-05 | New process for producing 6a,10a-cys-hexahydro-dibenzopiranones |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU77EI751A HU177307B (en) | 1976-07-06 | 1977-07-05 | New process for producing 6a,10a-cys-hexahydro-dibenzopiranones |
Country Status (30)
| Country | Link |
|---|---|
| US (2) | US4054581A (en:Method) |
| JP (2) | JPS5943465B2 (en:Method) |
| AR (1) | AR221210A1 (en:Method) |
| AT (2) | AT353268B (en:Method) |
| AU (1) | AU509540B2 (en:Method) |
| BE (1) | BE856408A (en:Method) |
| BG (2) | BG28564A4 (en:Method) |
| CA (1) | CA1090813A (en:Method) |
| CH (1) | CH633791A5 (en:Method) |
| CS (1) | CS196374B2 (en:Method) |
| DD (2) | DD137228A5 (en:Method) |
| DE (2) | DE2759994C2 (en:Method) |
| DK (1) | DK144885C (en:Method) |
| ES (2) | ES460381A1 (en:Method) |
| FR (1) | FR2361384A1 (en:Method) |
| GB (1) | GB1582565A (en:Method) |
| GR (1) | GR66413B (en:Method) |
| HU (2) | HU183288B (en:Method) |
| IE (1) | IE45242B1 (en:Method) |
| IL (1) | IL52423A (en:Method) |
| NL (1) | NL180316C (en:Method) |
| NZ (1) | NZ184530A (en:Method) |
| PH (2) | PH12637A (en:Method) |
| PL (1) | PL105356B1 (en:Method) |
| PT (1) | PT66742B (en:Method) |
| RO (1) | RO78107A (en:Method) |
| SE (2) | SE428016B (en:Method) |
| SU (2) | SU910121A3 (en:Method) |
| YU (1) | YU163277A (en:Method) |
| ZA (1) | ZA773955B (en:Method) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4054581A (en) * | 1976-07-06 | 1977-10-18 | Eli Lilly And Company | Preparation of cis-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-ones and intermediates therefor |
| US4133816A (en) * | 1977-07-12 | 1979-01-09 | Eli Lilly And Company | Preparation of cis-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-ones and intermediates therefor |
| US4171315A (en) * | 1978-03-31 | 1979-10-16 | Eli Lilly And Company | Preparation of cis-hexahydrodibenzopyranones |
| US4395560A (en) * | 1982-05-24 | 1983-07-26 | Eli Lilly And Company | Preparation of 6a,10a-trans-hexahydrodibenzopyranones |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3576887A (en) * | 1967-05-01 | 1971-04-27 | American Home Prod | Process for the preparation of oxaphenanthrenes and intermediates therefor |
| US3906047A (en) * | 1971-06-14 | 1975-09-16 | Hoffmann La Roche | 8-(2,6,6-Trimethyl-4-oxo-2-cyclohexen-1-ylidene-2-methylene-6-methyl-4,6-octadien-3-ol |
| US3929835A (en) * | 1973-08-29 | 1975-12-30 | Sharps Ass | Alkyl substituted cyclopenta benzopyrans |
| US3928598A (en) * | 1973-11-05 | 1975-12-23 | Lilly Co Eli | Hexahydro-dibenzo{8 b,d{9 pyran-9-ones as an anti-anxiety drug |
| US3968125A (en) * | 1973-11-05 | 1976-07-06 | Eli Lilly And Company | Dihydroxyhexahydrodibenzo[b,d]pyrans |
| US4054581A (en) * | 1976-07-06 | 1977-10-18 | Eli Lilly And Company | Preparation of cis-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-ones and intermediates therefor |
-
1976
- 1976-07-06 US US05/702,804 patent/US4054581A/en not_active Expired - Lifetime
-
1977
- 1977-06-29 GB GB27139/77A patent/GB1582565A/en not_active Expired
- 1977-06-30 NZ NZ184530A patent/NZ184530A/xx unknown
- 1977-06-30 PT PT66742A patent/PT66742B/pt unknown
- 1977-06-30 ZA ZA00773955A patent/ZA773955B/xx unknown
- 1977-06-30 CA CA281,764A patent/CA1090813A/en not_active Expired
- 1977-06-30 IL IL52423A patent/IL52423A/xx unknown
- 1977-06-30 SE SE7707629A patent/SE428016B/xx not_active IP Right Cessation
- 1977-06-30 PH PH19936A patent/PH12637A/en unknown
- 1977-07-01 DE DE2759994A patent/DE2759994C2/de not_active Expired
- 1977-07-01 YU YU01632/77A patent/YU163277A/xx unknown
- 1977-07-01 BG BG037943A patent/BG28564A4/xx unknown
- 1977-07-01 AU AU26680/77A patent/AU509540B2/en not_active Expired
- 1977-07-01 DE DE2729846A patent/DE2729846C2/de not_active Expired
- 1977-07-01 BG BG036779A patent/BG28062A3/xx unknown
- 1977-07-04 PL PL1977199365A patent/PL105356B1/pl unknown
- 1977-07-04 BE BE1008242A patent/BE856408A/xx not_active IP Right Cessation
- 1977-07-04 AR AR268306A patent/AR221210A1/es active
- 1977-07-04 CH CH818977A patent/CH633791A5/de not_active IP Right Cessation
- 1977-07-04 ES ES460381A patent/ES460381A1/es not_active Expired
- 1977-07-04 JP JP52081484A patent/JPS5943465B2/ja not_active Expired
- 1977-07-04 ES ES460382A patent/ES460382A1/es not_active Expired
- 1977-07-04 SU SU772497360A patent/SU910121A3/ru active
- 1977-07-05 GR GR53875A patent/GR66413B/el unknown
- 1977-07-05 DK DK301177A patent/DK144885C/da active
- 1977-07-05 DD DD77206148A patent/DD137228A5/xx unknown
- 1977-07-05 HU HU81128A patent/HU183288B/hu unknown
- 1977-07-05 RO RO7798722A patent/RO78107A/ro unknown
- 1977-07-05 IE IE1384/77A patent/IE45242B1/en unknown
- 1977-07-05 FR FR7720640A patent/FR2361384A1/fr active Granted
- 1977-07-05 NL NLAANVRAGE7707465,A patent/NL180316C/xx not_active IP Right Cessation
- 1977-07-05 HU HU77EI751A patent/HU177307B/hu unknown
- 1977-07-05 DD DD7700199901A patent/DD132495A5/xx unknown
- 1977-07-06 AT AT483277A patent/AT353268B/de not_active IP Right Cessation
- 1977-07-06 CS CS774514A patent/CS196374B2/cs unknown
- 1977-07-12 US US05/814,817 patent/US4115403A/en not_active Expired - Lifetime
- 1977-11-18 PH PH20451A patent/PH13260A/en unknown
-
1978
- 1978-07-06 SU SU782632856A patent/SU778712A3/ru active
- 1978-12-19 AT AT908478A patent/AT355019B/de not_active IP Right Cessation
-
1980
- 1980-07-24 SE SE8005373A patent/SE435060B/sv not_active IP Right Cessation
-
1981
- 1981-02-17 JP JP56022855A patent/JPS6049196B2/ja not_active Expired
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