Hydrochloric Acid → HCID 20315344, compound

HRID 1732391Notes

Reaction equation

HRID 1732391 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:9]=1[CH2:10][CH:11]([CH2:15][CH2:16][CH2:17][CH3:18])[C:12](O)=[O:13].Cl>C1COCC1>[Cl:7][C:8]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:9]=1[CH2:10][CH:11]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:12][OH:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 20306122HCID 20306122, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 20315344HCID 20315344, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 9.4 g (0.248 mole) of lithium aluminum hydride in 600 ml of THF is slowly added, at less than 10°; 46.0 g of the crude α-(2,4-dichlorobenzyl) hexanoic acid. The reaction is allowed to stir, and slowly warm up to ambient temperature. After 2 hours, the slurry is heated to reflux and held there for 16 hours. At the end of this period, the reaction is cooled and carefully poured into ice water to decompose the excess LiAlH4. The mixture is then made acidic by treatment with concentrated hydrochloric acid. The ether solution is separated, and the aqueous phase is extracted three times with 200 ml of ether. The extracts and the ether solution are combined and washed with 100 ml of dilute sodium bicarbonate solution and then with 100 ml of water. The solution is dried over anhydrous magnesium sulfate and the ether is stripped off to give 35.9 g of the crude alcohol product. Distillation (86.8°/0.15 mm) provides 34.2 g (93%) of pure alcohol. The material is identified by ir and its purity is determined by glc.

Workup

  1. temperaturethe slurry is heated
  2. temperatureto reflux
  3. waitheld there for 16 hours
  4. temperatureAt the end of this period, the reaction is cooled
  5. customThe ether solution is separated
  6. extractionthe aqueous phase is extracted three times with 200 ml of ether
  7. washwashed with 100 ml of dilute sodium bicarbonate solution
  8. dry with materialThe solution is dried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-374a758828e3421692c55c00f5a76e21
Source dataset
uspto-grants-1980_12
Patent number
US04237158

Reaction notes

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