Acetic Acid → HCID 15405234, compound

HRID 443194Notes

Reaction equation

HRID 443194 reaction equation
[CH3:1][O-:2].[Na+].[CH3:4][OH:5].[O:6]1[CH2:16][C:7]1([CH3:17])[CH:8]1C[CH2:12][CH:11]([CH3:14])[CH:10](O)[CH2:9]1.C(O)(=O)C>CO>[CH3:1][O:2][CH2:16][C:7]([OH:6])([CH3:17])[CH:8]1[CH2:9][CH2:10][CH:11]([CH3:14])[CH2:12][CH:4]1[OH:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 23694274Sodium methanolate methanolHCID 24976687HCID 24976687, compound

Product 1

HCID 15405234HCID 15405234, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Into a solution of a 28% sodium methylate-methanol solution (19.2 g; 0.1mol) in methanol (22ml) was added dropwise a solution of 8,9-epoxy-p-menthan-2-ol (17 g; 0.1 mol) in methanol (10 ml) with heating under reflux for over one hour. Upon completion, the resultant mixture was stirred at the same temperature for 3 hours for reaction. After cooling, glacial acetic acid (6.6 g; 0.11 mol) was added dropwise to the mixture for neutralizing the alkali. The oil layer which had been separated by adding chilled water was extracted with toluene, washed with brine until neutral, dried over anhydrous magnesium sulfate and concentrated under a low vacuum while recovering the toluene to give a crude product (17 g). The crude product was distilled under a high vacuum at a boiling point of 114° to 150° C./0.9 mm Hg to give the title compound (5) (15.2 g) (Theoretical yield: 75%). Analytical results on the title compound are given below.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for over one hour
  3. temperatureAfter cooling
  4. customThe oil layer which had been separated
  5. additionby adding
  6. temperaturechilled water
  7. extractionwas extracted with toluene
  8. washwashed with brine until neutral,
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under a low vacuum
  11. customwhile recovering the toluene
  12. customto give a crude product (17 g)
  13. distillationThe crude product was distilled under a high vacuum at a boiling point of 114° to 150° C./0.9 mm Hg

Sources & evidence

ORD record
ord-955b4245ecff46c7a363a10931de1344
Source dataset
uspto-grants-1999_04
Patent number
US05892133

Reaction notes

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