Sulfuric Acid → HCID 15125089, compound

HRID 373372Notes

Reaction equation

HRID 373372 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH2:9][C:10](O)=[O:11])=[C:4]([CH3:13])[C:3]=1[CH3:14].[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O>O1CCCC1>[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH2:9][CH2:10][OH:11])=[C:4]([CH3:13])[C:3]=1[CH3:14]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 15125088HCID 15125088, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15125089HCID 15125089, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4-hydroxy-2,3,6-trimethylphenyl-acetic acid (2.5 g) in anhydrous tetrahydrofuran (20 ml) was added lithium aluminum hydride (0.5 g) at 0° C. and the mixture was heated at 40° C. for 3 hours. The mixture was cooled to 0° C. Diluted sulfuric acid was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated saline and dried with anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure to obtain 2-(4-hydroxy-2,3,6-trimethylphenyl)ethanol (2.3 g) (Compound A-24). The physical properties and NMR spectrum data thereof are shown in Table 1.

Workup

  1. temperatureThe mixture was cooled to 0° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated saline
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cc10fe7314974428915191dd900cce1a
Source dataset
uspto-grants-1992_11
Patent number
US05162571

Reaction notes

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