Toluene → HCID 13103211, compound

HRID 2083400Notes

Reaction equation

HRID 2083400 reaction equation
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH3:7])[C:4](=[O:6])[CH3:5].[CH3:10][N:11]([CH3:20])[C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O>[CH3:10][N:11]([CH3:20])[C:12]1[CH:19]=[CH:18][C:15]([CH:16]2[O:9][CH2:8][C:3]([C:4]([CH3:5])=[O:6])([CH3:7])[CH2:2][O:1]2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 74794-(Dimethylamino)BenzaldehydeHCID 5365163,3-Bis(hydroxymethyl)-2-butanone

Product 1

HCID 13103211HCID 13103211, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

3,3-bis(Hydroxymethyl)butanone (29.0 g), p-dimethylaminobenzaldehyde (29.8 g), toluene-p-sulphonic acid (250 mg) and toluene (140 ml) were heated under reflux in a Dean and Stark water trap until the theoretical amount of water had separated. The solution was concentrated in vacuo, the crude residue was washed with 8% aqueous sodium bicarbonate solution (100 ml) and crystallised from petroleum ether (b.p. 80°-100°)/ethyl acetate as a crystalline solid m.p.118°-120° (Cis-trans 96:4).

Workup

  1. customhad separated
  2. concentrationThe solution was concentrated in vacuo
  3. washthe crude residue was washed with 8% aqueous sodium bicarbonate solution (100 ml)
  4. customcrystallised from petroleum ether (b.p. 80°-100°)/ethyl acetate as a crystalline solid m.p.118°-120° (Cis-trans 96:4)

Sources & evidence

ORD record
ord-3d9446bb3c7544949536284add1db1f2
Source dataset
uspto-grants-1978_04
Patent number
US04085222

Reaction notes

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