Water → HCID 12953785, compound

HRID 1703190Notes

Reaction equation

HRID 1703190 reaction equation
[O:1]=[C:2]([C:5]1[C:6]([C:15](O)=[O:16])=[CH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:3][CH3:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1>[OH:16][CH2:15][C:6]1[C:5]([CH:2]([OH:1])[CH2:3][CH3:4])=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 12953784HCID 12953784, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12953785HCID 12953785, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The above carboxylic acid (11 g) in THF (150 ml) was added to lithium aluminium hydride (6.0 g) in THF (150 ml) over 0.5 hr. The reaction mixture was stirred for 2 hr. and water was carefully added. The resultant slurry was washed with ether (3×100 ml) and the combined ethereal washings were dried (magnesium sulphate) and evaporated to dryness to give 2-hydroxymethyl-3-(1'-hydroxypropyl)naphthalene as an oil; a small portion was recrystallised from light petroleum (b.p. 60°-80°)/chloroform to give a crystalline solid, m.p. 70°.

Workup

  1. washThe resultant slurry was washed with ether (3×100 ml)
  2. dry with materialthe combined ethereal washings were dried (magnesium sulphate)
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-f0ae1a4aa56d418fa5be0e337d48a98c
Source dataset
uspto-grants-1982_09
Patent number
US04351842

Reaction notes

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