Benzaldehyde → 1,3-Dioxan-5-ol, 2-phenyl-

HRID 1779747Notes

Reaction equation

HRID 1779747 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][CH2:10][CH:11]([CH2:13]O)[OH:12].CC1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1.C(OC(C)C)(C)C>[OH:12][CH:11]1[CH2:10][O:9][CH:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[O:8][CH2:13]1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 753GlycerolHCID 962Water2×HCID 6101p-Toluenesulfonic acid

Product 1

HCID 743621,3-Dioxan-5-ol, 2-phenyl-

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7914Diisopropyl EtherSolvent

Procedure

To a solution of benzaldehyde (150.0 g, 1.41 mol) in toluene, glycerol (160.0 g, 1.74 mol) was added followed by 4-methylbenzenesulfonic acid (1.0 g) and the mixture was vigorously stirred under reflux with a Dean-Stark water separator. The refluxing was continued until no more water separated in the condenser (6-8 h). The clear solution was treated with 4N NaOH until basic and the organic layer was washed with water (5×100 mL) followed by saturated sodium chloride solution and then dried over anhydrous sodium sulfate. Concentration of the organic layer resulted in an oil which was dissolved in hot isopropylether and then left in the freezer overnight. The colorless solid was filtered and washed with isopropylether to yield the title product as a colorless solid. Yield: 55.0 g (22%). m.p. 83°-84° C. [Lit. m.p. 83°-84° C.; J. S. Briamacombe, A. B. Foster and M. Stacey, Chem. & Ind., 1958, 122814 9]. 1H NMR (CDCl3) ε 3.1 (d, 1H, --OH), 3.7 (d, 1H Ar--CH), 4.3 (m, 4H, O--CH2), 5.6 (s, 1H, O--CH--O) and 7.4 (m, 5H, Ar--H). M/e: [M+H]+ =181.

Workup

  1. customseparated in the condenser (6-8 h)
  2. additionThe clear solution was treated with 4N NaOH until basic and the organic layer
  3. washwas washed with water (5×100 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customConcentration of the organic layer resulted in an oil which
  6. filtrationThe colorless solid was filtered
  7. washwashed with isopropylether

Sources & evidence

ORD record
ord-bf642565fb3241aabc99c64ad4b1b630
Source dataset
uspto-grants-1997_05
Patent number
US05627286

Reaction notes

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