FR2424898A1 - Prepn. of i-phenyl cyclopentane carboxylic acid - by reaction of phenyl acetonitrile with a butane di:halide, followed by hydrolysis - Google Patents
Prepn. of i-phenyl cyclopentane carboxylic acid - by reaction of phenyl acetonitrile with a butane di:halide, followed by hydrolysisInfo
- Publication number
- FR2424898A1 FR2424898A1 FR7813038A FR7813038A FR2424898A1 FR 2424898 A1 FR2424898 A1 FR 2424898A1 FR 7813038 A FR7813038 A FR 7813038A FR 7813038 A FR7813038 A FR 7813038A FR 2424898 A1 FR2424898 A1 FR 2424898A1
- Authority
- FR
- France
- Prior art keywords
- phenyl
- carboxylic acid
- butane
- prepn
- halide
- 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.)
- Withdrawn
Links
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 title abstract 4
- 239000001273 butane Substances 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 title 1
- 150000004820 halides Chemical class 0.000 title 1
- 230000007062 hydrolysis Effects 0.000 title 1
- 238000006460 hydrolysis reaction Methods 0.000 title 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 title 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 title 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 abstract 1
- GDXMFFGTPGAGGX-UHFFFAOYSA-N 1-phenylcyclopentane-1-carbonitrile Chemical compound C=1C=CC=CC=1C1(C#N)CCCC1 GDXMFFGTPGAGGX-UHFFFAOYSA-N 0.000 abstract 1
- RHPCYZLXNNRRMB-UHFFFAOYSA-N 1-phenylcyclopentane-1-carboxylic acid Chemical compound C=1C=CC=CC=1C1(C(=O)O)CCCC1 RHPCYZLXNNRRMB-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 150000001414 amino alcohols Chemical class 0.000 abstract 1
- 230000000954 anitussive effect Effects 0.000 abstract 1
- 230000002921 anti-spasmodic effect Effects 0.000 abstract 1
- 229940124575 antispasmodic agent Drugs 0.000 abstract 1
- 239000003434 antitussive agent Substances 0.000 abstract 1
- 229940124584 antitussives Drugs 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1-Phenyl cyclopentane carboxylic acid (I) is prepd. by the alkylation of phenylacetonitrile (II) with a dihalide X(CH2)4X (III) (where X = halogen) in aq. NaOH and DMSO and the prod., 1-phenyl cyclopentane carbonitrile is hydrolysed to (I) is an acid medium at >=120 degrees C. Esters of (I) with aminoalcohols are antispasmodics and antitussives. The process is simple and economical to carry out, and gives good yields. The molar ratio (II):(III) is preferably 1:1, 1,4-dibromo butane being the pref. dihalide (III). The sodium hydroxide soln. usually contains 300-500g per kg and the weight ratio of (II) : DMSO is generally within the range 1 : 1 to 1 : 2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7813038A FR2424898A1 (en) | 1978-05-03 | 1978-05-03 | Prepn. of i-phenyl cyclopentane carboxylic acid - by reaction of phenyl acetonitrile with a butane di:halide, followed by hydrolysis |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7813038A FR2424898A1 (en) | 1978-05-03 | 1978-05-03 | Prepn. of i-phenyl cyclopentane carboxylic acid - by reaction of phenyl acetonitrile with a butane di:halide, followed by hydrolysis |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2424898A1 true FR2424898A1 (en) | 1979-11-30 |
Family
ID=9207847
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7813038A Withdrawn FR2424898A1 (en) | 1978-05-03 | 1978-05-03 | Prepn. of i-phenyl cyclopentane carboxylic acid - by reaction of phenyl acetonitrile with a butane di:halide, followed by hydrolysis |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2424898A1 (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH518252A (en) * | 1968-07-04 | 1972-01-31 | Takeda Chemical Industries Ltd | Process for the preparation of cycloalkanecarboxylic acids |
| US3755412A (en) * | 1969-07-07 | 1973-08-28 | Exxon Research Engineering Co | Alkylation of acetonitriles |
| JPS5138709A (en) * | 1974-09-30 | 1976-03-31 | Komatsu Mfg Co Ltd | KOSHITSUGANBANNORITSUPINGUHOHO |
-
1978
- 1978-05-03 FR FR7813038A patent/FR2424898A1/en not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH518252A (en) * | 1968-07-04 | 1972-01-31 | Takeda Chemical Industries Ltd | Process for the preparation of cycloalkanecarboxylic acids |
| US3755412A (en) * | 1969-07-07 | 1973-08-28 | Exxon Research Engineering Co | Alkylation of acetonitriles |
| JPS5138709A (en) * | 1974-09-30 | 1976-03-31 | Komatsu Mfg Co Ltd | KOSHITSUGANBANNORITSUPINGUHOHO |
Non-Patent Citations (2)
| Title |
|---|
| CA1975 * |
| CA1977 * |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |