Hydrochloric Acid → 2-[4-(2-Hydroxycyclohexylidenemethyl)phenyl]propionic acid

HRID 1462934ノート

反応式

HRID 1462934 の反応式
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1.C([BH3-])#N.[Na+].Cl.[Cl-].[Na+]>CO>[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[CH:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])=[CH:13][CH:14]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 1296782-[4-(2-Oxocyclohexylidenemethyl)phenyl]propionic acidHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 537414562-[4-(2-Hydroxycyclohexylidenemethyl)phenyl]propionic acid

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

2 g of 2-[4-(2-oxocyclohexylidenemethyl)phenyl]propionic acid (which may be prepared as described in United Kingdom Patent Specification No. 2,002,762) and 0.6 g of sodium cyanoborohydride were dissolved in 40 ml of methanol. The pH of the solution was adjusted to a value of 3 by the addition of 6N hydrochloric acid, whilst ice-cooling. The mixture was then heated under reflux for 1 hour, after which a saturated aqueous solution of sodium chloride was added and the mixture was extracted with diethyl ether. The extract was dried and the solvent was then distilled off. The residue was purified by high speed liquid chromatography, to give the desired compound in a crude form. This was recrystallised from a 1:1 by volume mixture of ethyl acetate and hexane, to give 350 mg of the title compound, melting at 135°-136° C.

後処理

  1. temperaturecooling
  2. temperatureThe mixture was then heated
  3. temperatureunder reflux for 1 hour
  4. extractionthe mixture was extracted with diethyl ether
  5. customThe extract was dried
  6. distillationthe solvent was then distilled off
  7. customThe residue was purified by high speed liquid chromatography

出典と根拠

ORDレコード
ord-4a10b45458a84697b0da85a6ac77e14d
出典データセット
uspto-grants-1984_07
特許番号
US04461912

反応ノート

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