Aluminium lithium hydride → 2-Chloro-4-mercaptophenol

HRID 68230Notes

Reaction equation

HRID 68230 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[C:10]([S:15]C#N)[CH:11]=[CH:12][C:13]=1[OH:14]>O1CCCC1>[Cl:7][C:8]1[CH:9]=[C:10]([SH:15])[CH:11]=[CH:12][C:13]=1[OH:14]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 596017022-Chloro-4-thiocyanatophenol

Product 1

HCID 143697432-Chloro-4-mercaptophenolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminium hydride (as a 1M solution in tetrahydrofuran, 71.0 ml, 71.0 mmol) was added dropwise to an ice cold solution of 3-chloro-4-hydroxyphenyl thiocyanate (4.20 g, 22.6 mmol) in tetrahydrofuran (100 mL) under nitrogen. The reaction mixture was stirred and allowed to warm to room temperature over 5 hours. The mixture was cooled to 5° C. and quenched with a 1:1 mixture of tetrahydrofuran:water until no more gas evolution was seen. 1N hydrochloric acid solution in water (30 mL) was then added, and the mixture extracted with ethyl acetate (2-fold 70 mL). The combined organic layers were dried (sodium sulphate) and concentrated in vacuo affording a colourless crystalline solid, 100% yield, 3.60 g.

Workup

  1. temperatureThe mixture was cooled to 5° C.
  2. customquenched with a 1:1 mixture of tetrahydrofuran
  3. addition1N hydrochloric acid solution in water (30 mL) was then added
  4. extractionthe mixture extracted with ethyl acetate (2-fold 70 mL)
  5. dry with materialThe combined organic layers were dried (sodium sulphate)
  6. concentrationconcentrated in vacuo
  7. customaffording a colourless crystalline solid, 100% yield, 3.60 g

Sources & evidence

ORD record
ord-80938e306ddf4358b1a02ccf299ce800
Source dataset
uspto-grants-2014_09
Patent number
US08822439B2

Reaction notes

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