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

HRID 34846Notes

Reaction equation

HRID 34846 reaction equation
[CH2:1]([C:7]1[CH:21]=[C:20]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:19]=[CH:18][C:8]=1[O:9][CH2:10][CH:11]1[CH2:15][O:14]C(C)(C)[O:12]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].Cl>O1CCCC1>[CH2:1]([C:7]1[CH:21]=[C:20]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:19]=[CH:18][C:8]=1[O:9][CH2:10][CH:11]([OH:12])[CH2:15][OH:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 148196694-((2-Hexyl-4-tetradecylphenoxy)methyl)-2,2-dimethyl-1,3-dioxolane

Product 1

HCID 148196703-(2-Hexyl-4-tetradecylphenoxy)-1,2-propanediolYield 98.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 13.6 g of 4-[(2-hexyl-4-tetradecylphenoxy)methyl]-2,2-dimethyl-1,3-dioxolane, 10 ml of 5% hydrochloric acid and 250 ml of tetrahydrofuran was heated at reflux for 4 hours, then allowed to cool and the tetrahydrofuran removed under reduced pressure. The mixture was then extracted several times with ethyl acetate. The organic extracts were combined, washed with aqueous sodium bicarbonate, dried and the solvent evaporated, giving 12.3 g of the desired compound.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. temperatureto cool
  4. customthe tetrahydrofuran removed under reduced pressure
  5. extractionThe mixture was then extracted several times with ethyl acetate
  6. washwashed with aqueous sodium bicarbonate
  7. customdried
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-711ef3573cc442a582daacab3d201232
Source dataset
uspto-grants-1988_08
Patent number
US04762942

Reaction notes

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