Hydrochloric Acid → 3-(2-Ethyl-5-tetradecylphenoxy)1,2-propanediol

HRID 34855Notes

Reaction equation

HRID 34855 reaction equation
[CH2:1]([C:3]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:14][C:4]=1[O:5][CH2:6][CH:7]1[CH2:11][O:10]C(C)(C)[O:8]1)[CH3:2].Cl>O1CCCC1>[CH2:1]([C:3]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:14][C:4]=1[O:5][CH2:6][CH:7]([OH:8])[CH2:11][OH:10])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 148196794-((2-Ethyl-5-tetradecylphenoxy)methyl)-2,2-dimethyl-1,3-dioxolane

Product 1

HCID 142562013-(2-Ethyl-5-tetradecylphenoxy)1,2-propanediol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 14.2 g of 4-[(2-ethyl-5-tetradecylphenoxy)methyl]-2,2-dimethyl-1,3-dioxolane, 50 ml of 5% hydrochloric acid and 100 ml of tetrahydrofuran was heated at reflux for 8 hours, then allowed to cool and the tetrahydrofuran removed under reduced pressure. Ethyl acetate was added, the mixture washed with water, dried and the solvents removed. The residue was chromatographed on silica gel, eluting impurites with hexane:ethyl acetate (16:1) and then (4:1) to elute the desired compound, giving 11 g, 55.5°-56.5° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 hours
  3. temperatureto cool
  4. customthe tetrahydrofuran removed under reduced pressure
  5. additionEthyl acetate was added
  6. washthe mixture washed with water
  7. customdried
  8. customthe solvents removed
  9. customThe residue was chromatographed on silica gel
  10. washeluting impurites with hexane:ethyl acetate (16:1)
  11. wash(4:1) to elute the desired compound
  12. customgiving 11 g, 55.5°-56.5° C.

Sources & evidence

ORD record
ord-ded692c36d62480a812fefe12a071ecc
Source dataset
uspto-grants-1988_08
Patent number
US04762942

Reaction notes

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