HCID 178521094, compound → (2R)-3-(4-benzyloxyphenoxy)-1,2-propanediol

HRID 2417979Notes

Reaction equation

HRID 2417979 reaction equation
[CH2-]C(C)=O.[CH2:5]([O:12][C:13]1[CH:24]=[CH:23][C:16]([O:17][CH2:18][C@@H:19]([OH:22])[CH2:20][OH:21])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>O>[CH2:5]([O:12][C:13]1[CH:14]=[CH:15][C:16]([O:17][CH2:18][C@H:19]([OH:22])[CH2:20][OH:21])=[CH:23][CH:24]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

3

Reactant 1

HCID 178521094HCID 178521094, compound

Product 1

HCID 13061877(2R)-3-(4-benzyloxyphenoxy)-1,2-propanediol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The methanolic solution of (2S)-3-(4-benzyloxyphenoxy)-1,2-propanediol acetonide (~2 L) from the previous example was diluted with 120 ml water and combined with Dowex 50W-8X ion exchange resin (50 ml) in a flask fitted for distillation. The stirred mixture was heated to boiling and 1.8 L of distillate was collected over 3 hours. The reaction was diluted with ethanol (500 ml) and benzene (500 ml) filtered free of the resin and concentrated to dryness in vacuo. The residue was crystallized from ether and from ethyl acetate to give 137.0 g of (2R)-3-(4-benzyloxyphenoxy)-1,2-propanediol in several crops.

Workup

  1. customfitted for distillation
  2. temperatureThe stirred mixture was heated
  3. distillation1.8 L of distillate was collected over 3 hours
  4. additionThe reaction was diluted with ethanol (500 ml) and benzene (500 ml)
  5. filtrationfiltered free of the resin
  6. concentrationconcentrated to dryness in vacuo
  7. customThe residue was crystallized from ether and from ethyl acetate

Sources & evidence

ORD record
ord-41c175a6bea34428b4469e1a47b0894e
Source dataset
uspto-grants-1984_09
Patent number
US04471116

Reaction notes

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