Sulfuric Acid → Carvacrol

HRID 273664

Reaction equation

HRID 273664 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]1[C:12](=[O:13])[CH2:11][CH:10]([C:14]([CH3:16])=[CH2:15])[CH2:9][CH:8]=1.CN(CC1C2C=CC=CC=2NC=1)C>>[CH:11]1[C:10]([CH:14]([CH3:16])[CH3:15])=[CH:9][CH:8]=[C:7]([CH3:6])[C:12]=1[OH:13]

Participants

4

Reactant 3

HCID 1118Sulfuric Acid2×HCID 6890GramineHCID 7439Carvone, (+-)-

Product 1

HCID 10364Carvacrol

Procedure

Aqueous 0.5M sulphuric acid (25 ml), Teric N100 emulsifying agent (a product of ICI; 2.5 g) and carvone (50 g) were stirred and the emulsion passed through the CMR four times (15.5 ml/min, 165°-75° C., 690-760 kPa). Analysis was again by GC after each pass. After four passes a conversion of 50% was obtained. This experiment was then repeated using 1M sulphuric acid, and was directly comparable with experiment (a) above, the variation being the addition of the emulsifying agent. After four successive passes, the percentage of carvacrol obtained was 32%, 63%, 73% and 83%, with negligible by-product formation.

Workup

  1. custompassed through the CMR four times (15.5 ml/min, 165°-75° C., 690-760 kPa)
  2. customAfter four passes a conversion of 50% was obtained
  3. additionthe addition of the emulsifying agent

Sources & evidence

ORD record
ord-05facc1ee4584e22b59f4faba79225cf
Source dataset
uspto-grants-1995_02
Patent number
US05387397

Linked notes

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