Potassium Carbonate → HCID 15117874, compound

HRID 2107747Notes

Reaction equation

HRID 2107747 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:17])[CH3:16])=[CH:11][C:10]=1[OH:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:24]1[C:26]([CH3:31])([CH2:27][CH2:28][CH:29]=[CH2:30])[CH2:25]1.C(=O)([O-])[O-].[K+].[K+]>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:16])[CH3:17])=[CH:11][C:10]=1[O:23][CH2:25][C:26]([OH:24])([CH3:31])[CH2:27][CH2:28][CH:29]=[CH2:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 147403841,2-Epoxy-2-methyl-5-hexeneHCID 15117873HCID 15117873, compound

Product 1

HCID 15117874HCID 15117874, compoundYield 82.8%

Conditions

Temperature
120 °C

Procedure

A mixture of 7.4 g (23.7 mmole) of 2-benzyloxy-5-t-octylphenol, 5.3 g (47.4 mmole) of 1,2-epoxy-2-methyl-5-hexene and 3.27 g (23.7 mmole) of potassium carbonate was heated at 120° C., with stirring, under nitrogen, for 48 hours. The cooled reaction mixture was extracted with ethyl acetate, and the resulting solution was washed with water followed by saturated sodium chloride solution. Evaporation of the washed ethyl acetate solution in vacuo, followed by purification of the residue by column chromatography on silica gel, eluting with 9:1 toluene-ethyl acetate, gave 8.33 g of the title compound as an oil.

Workup

  1. customThe cooled reaction mixture
  2. extractionwas extracted with ethyl acetate
  3. washthe resulting solution was washed with water
  4. customEvaporation of the washed ethyl acetate solution in vacuo
  5. customfollowed by purification of the residue by column chromatography on silica gel
  6. washeluting with 9:1 toluene-ethyl acetate

Sources & evidence

ORD record
ord-e06899b5e715419d86d80ebb65029ac6
Source dataset
uspto-grants-1990_06
Patent number
US04935442

Reaction notes

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