Hydrochloric Acid → 112395-77-4

HRID 2166483Notes

Reaction equation

HRID 2166483 reaction equation
[CH2:1]([C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[OH:11])[CH:2]=C.[O:12]=[O+][O-].[BH4-].[Na+].Cl>CO>[OH:11][C:5]1[CH:6]=[CH:7][C:8]([CH3:10])=[CH:9][C:4]=1[CH2:1][CH2:2][OH:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24823OzoneHCID 811172-Allyl-p-cresolHCID 4311764Sodium borohydride

Product 1

HCID 15702966112395-77-4Yield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 8.34 g (0.05 mol) of 2-allyl-4-methylphenol in 420 ml of CH3OH containing a few crystals of Sudan III indicator was cooled to -78° C. Ozone was passed through this solution until a color change of the Sudan III indicator showed that the ozonization reaction was complete. Solid sodium borohydride (6.4 g) was added in small portions to the cold solution. When this addition was complete, the solution was allowed to warm to room temperature overnight. The solution was made acid by the addition of 6N HCl, and then was concentrated to dryness in vacuo. The residue was dissolved in ethyl acetate and was washed with water, saturated NaHCO3 solution and brine. The solution was dried, filtered, and evaporated to give 7.3 g (96%) of 2-(2-hydroxy-5-methylphenyl)ethanol.

Workup

  1. customshowed that the ozonization reaction
  2. additionWhen this addition
  3. concentrationwas concentrated to dryness in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwas washed with water, saturated NaHCO3 solution and brine
  6. customThe solution was dried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-42898d16be014a0fa9a08e4679987b34
Source dataset
uspto-grants-1990_07
Patent number
US04945182

Reaction notes

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