4-Hydroxybenzaldehyde → 4-[(2S,4R,5S)-5-octyl-4-methyl-1,3-dioxan-2-yl]phenol

HRID 440209Notes

Reaction equation

HRID 440209 reaction equation
[CH2:1]([C@H:9]([C@H:12]([OH:14])[CH3:13])[CH2:10][OH:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1.S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>C(OCC)C.O.C1(C)C=CC=CC=1>[CH2:1]([C@H:9]1[CH2:10][O:11][C@H:20]([C:19]2[CH:22]=[CH:23][C:16]([OH:15])=[CH:17][CH:18]=2)[O:14][C@@H:12]1[CH3:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

8

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 1118Sulfuric AcidHCID 516892Sodium Bicarbonate2×HCID 57227381(2S,3R)-2-octyl-1,3-butanediol

Product 1

HCID 677427334-[(2S,4R,5S)-5-octyl-4-methyl-1,3-dioxan-2-yl]phenolYield 84.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 320 mg of (2S,3R)-2-octyl-1,3-butanediol, 193 mg of p-hydroxybenzaldehyde, 0.1 ml of 1N sulfuric acid and 20 ml of toluene was placed under nitrogen in a round flask having a magnetic stirrer, water separator and condenser. The mixture was heated to reflux for 3 hours while separating water. The cooled reaction mixture was poured into aqueous sodium hydrogen carbonate solution and treated with diethyl ether. The aqueous phase was separated and extracted three times with diethyl ether. The combined organic phases were washed three times with round flask having a magnetic stirrer, water separator and condenser. The mixture was heated to reflux for 3 hours while separating water. The cooled reaction mixture was poured into aqueous sodium hydrogen carbonate solution and treated with diethyl ether. The aqueous phase was separated and extracted three times with diethyl ether. The combined organic phases were washed three times with water, dried over magnesium sulfate, filtered and evaporated. Recrystallization of the yellowish, solid residue (480 mg) from hexane/ethyl acetate (vol. 25:1) gave 410 mg of 4-[(2S,4R,5S)-5-octyl-4-methyl-1,3-dioxan-2-yl]phenol as yellowish crystals with [a]D =+27° (c=1% in chloroform).

Workup

  1. customwas placed under nitrogen in a round flask
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 3 hours
  4. customwhile separating water
  5. customThe cooled reaction mixture
  6. customThe aqueous phase was separated
  7. extractionextracted three times with diethyl ether
  8. washThe combined organic phases were washed three times with round flask
  9. temperatureThe mixture was heated
  10. temperatureto reflux for 3 hours
  11. customwhile separating water
  12. customThe cooled reaction mixture
  13. customThe aqueous phase was separated
  14. extractionextracted three times with diethyl ether
  15. washThe combined organic phases were washed three times with water
  16. dry with materialdried over magnesium sulfate
  17. filtrationfiltered
  18. customevaporated
  19. customRecrystallization of the yellowish, solid residue (480 mg) from hexane/ethyl acetate (vol. 25:1)

Sources & evidence

ORD record
ord-6bd2f73368e3422e80e59b95758b8842
Source dataset
uspto-grants-1996_05
Patent number
US05518653

Reaction notes

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