Hydrochloric Acid → 3-(2-Ethyl-4-tetradecylphenoxy)-1,2-propanediol

HRID 34840Notes

Reaction equation

HRID 34840 reaction equation
[CH2:1]([C:3]1[CH:17]=[C:16]([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:15]=[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]=[C:16]([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:15]=[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 142562074-((2-Ethyl-4-tetradecylphenoxy)methyl)-2,2-dimethyl-1,3-dioxolane

Product 1

HCID 142561973-(2-Ethyl-4-tetradecylphenoxy)-1,2-propanediolYield 85.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 15.55 g of 4-[(2-ethyl-4-tetradecylphenoxy)methyl]-2,2-dimethyl-1,3-dioxolane, 10 ml of 5% hydrochloric acid and 300 ml of tetrahydrofuran was heated at reflux for 4 hours, then cooled and 1/2 of the solvent evaporated at reduced pressure. The remainder was diluted with ethyl acetate, washed with aqueous sodium bicarbonate, dried and the solvents evaporated. The residue was chromatographed on silica gel, eluting first with hexane:ethyl acetate (8:1), then (4:1), giving 12.1 g of the desired compound, mp 55°-56° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. temperaturecooled
  4. custom1/2 of the solvent evaporated at reduced pressure
  5. additionThe remainder was diluted with ethyl acetate
  6. washwashed with aqueous sodium bicarbonate
  7. customdried
  8. customthe solvents evaporated
  9. customThe residue was chromatographed on silica gel
  10. washeluting first with hexane:ethyl acetate (8:1)

Sources & evidence

ORD record
ord-55ea2f5a14db439ca59cd47390d5c2c2
Source dataset
uspto-grants-1988_08
Patent number
US04762942

Reaction notes

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