Water → (3-Chloro-1,2-phenylene)dimethanol

HRID 1032687Notes

Reaction equation

HRID 1032687 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:18]=[CH:17][CH:16]=[C:10]2[C:11]([O:13][C:14](=O)[C:9]=12)=[O:12].O.[OH-].[Na+]>C(OCC)C.O1CCCC1>[OH:12][CH2:11][C:10]1[CH:16]=[CH:17][CH:18]=[C:8]([Cl:7])[C:9]=1[CH2:14][OH:13]

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 670143-Chlorophthalic anhydrideHCID 21226445Aluminium lithium hydride

Product 1

HCID 17862674(3-Chloro-1,2-phenylene)dimethanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5 g of lithium aluminium hydride in 50 ml of dry diethyl ether was added dropwise with stirring a solution of 10 g (54.8 mmole) of 3-chlorophthalic anhydride in 120 ml of dry tetrahydrofuran. After heating under reflux for 6 hours, the mixture was cooled and treated carefully with 5 ml of water, 5 ml of 10% sodium hydroxide solution and 10 ml of water. The solution was filtered, the filtrate was dried over magnesium sulphate, filtered and evaporated to yield the title compound as a colourless waxy solid.

Workup

  1. additionwas added dropwise
  2. temperatureAfter heating
  3. temperatureunder reflux for 6 hours
  4. temperaturethe mixture was cooled
  5. filtrationThe solution was filtered
  6. dry with materialthe filtrate was dried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-f885cce0699e427fa5f01768dc8eef08
Source dataset
uspto-grants-1990_09
Patent number
US04959374

Reaction notes

Loading…