Hydrochloric Acid → (2,6-Dimethylphenyl)methanol

HRID 345780Notes

Reaction equation

HRID 345780 reaction equation
C([O:3][C:4](=O)[C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:12])C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[H-].Cl>C(OCC)C.O>[CH3:12][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([CH3:11])[C:5]=1[CH2:4][OH:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 166653HydrideHCID 520807Ethyl 2,6-dimethylbenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 186748(2,6-Dimethylphenyl)methanolYield 77.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

17 g of 2,6-dimethyl benzoic acid ethyl ester (0.095 mole) dissolved in 50 ml of ethyl ether are added dropwise as a function of the vigor of reflux to a suspension of 3.72 g (0.095 mole) of LiAlH4 in 100 ml of ether. When the addition is complete, the mixture is heated at reflux for 2h and left to stand overnight. Excess hydride is decomposed by the gradual addition of water (while cooling the flask in an ice-water bath), then 10% HCl. After the usual work-up, the product is crystallized from petroleum ether. 10 g of product are obtained. M.p.=84°. Yield 77.5%.

Workup

  1. additionare added dropwise as a function of the vigor
  2. additionWhen the addition
  3. temperaturethe mixture is heated
  4. waitleft
  5. customAfter the usual work-up, the product is crystallized from petroleum ether

Sources & evidence

ORD record
ord-0da8fb96850b4fa4af3bae9273f05dea
Source dataset
uspto-grants-1991_10
Patent number
US05059614

Reaction notes

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