Diethyl Ether → HCID 53690970, compound

HRID 426772Notes

Reaction equation

HRID 426772 reaction equation
CCOCC.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([S:22][C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[C:17]([CH:21]=1)[C:18](O)=[O:19]>O>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([S:22][C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[C:17]([CH:21]=1)[CH2:18][OH:19]

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 826514HCID 826514, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 53690970HCID 53690970, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 30 ml of abs. ether cooled to 3° is added under nitrogen 1.14 g (0.03 mole) of lithium aluminium hydride, and there is then added dropwise at 5°-10° with stirring, within half an hour, a solution of 5.4 g (0.02 mole) of 5-chloro-2-(2-thienylthio)-benzoic acid (produced according to Swiss Patent Specification No. 405,354; C.A. 66, P 2550e) in 45 ml of abs. ether. After completion of the dropwise addition, the mixture is refluxed for 16 hours; and there is thereupon slowly added dropwise at 3°-7° 5 ml of water. The occurring precipitate is filtered off with suction, and subsequently well washed with ether. The filtrate is concentrated in vacuo, and the residue is recrystallised from carbon tetrachloride to yield 5-chloro-2-(2-thienylthio)-benzyl alcohol having a melting point of 95°-96°.

Workup

  1. additionis then added dropwise at 5°-10°
  2. additionAfter completion of the dropwise addition
  3. temperaturethe mixture is refluxed for 16 hours
  4. filtrationThe occurring precipitate is filtered off with suction
  5. washsubsequently well washed with ether
  6. concentrationThe filtrate is concentrated in vacuo
  7. customthe residue is recrystallised from carbon tetrachloride

Sources & evidence

ORD record
ord-bc653bb388374d329583769a6d701654
Source dataset
uspto-grants-1979_10
Patent number
US04171366

Reaction notes

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