Water → HCID 21276841, compound

HRID 2292113Notes

Reaction equation

HRID 2292113 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[C:10]([C:20](OCC)=[O:21])[C:11](=[CH:18][CH:19]=1)[CH2:12][C:13](OCC)=[O:14].O>CCOCC>[Cl:7][C:8]1[CH:9]=[C:10]([CH2:20][OH:21])[C:11]([CH2:12][CH2:13][OH:14])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydride2×HCID 21276877HCID 21276877, compound

Product 1

HCID 21276841HCID 21276841, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Lithium aluminium hydride (12 g) was suspended in dry ether (500 ml). A solution of diethyl 4-chlorohomophthalate (75 g) in ether (200 ml) was added dropwise to the above suspension over 30 minutes. The reaction mixture was heated at reflux for 2 hrs. Excess lithium aluminium hydride was decomposed carefully with water and the resulting mixture filtered through a pad of diatomaceous earth. The filtrate was partitioned between water (200 ml) and ether (800 ml). The organic layer was dried (magnesium sulphate) and evaporated in vacuo to a semi-solid which on trituation with petroleum ether (b.pt. 40°-60°) gave 2-(4-chloro-6-hydroxymethylphenyl)ethanol as a solid (45 g) m.pt. 75°-76°, characterised by its nmr spectrum.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 hrs
  3. filtrationthe resulting mixture filtered through a pad of diatomaceous earth
  4. customThe filtrate was partitioned between water (200 ml) and ether (800 ml)
  5. dry with materialThe organic layer was dried (magnesium sulphate)
  6. customevaporated in vacuo to a semi-solid which on trituation with petroleum ether (b.pt. 40°-60°)

Sources & evidence

ORD record
ord-d5d39b71c9164355aacffb85063b094c
Source dataset
uspto-grants-1989_01
Patent number
US04801593

Reaction notes

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