HCID 13755497, compound → HCID 13755499, compound

HRID 979892Notes

Reaction equation

HRID 979892 reaction equation
C([O:8][CH2:9][C@H:10]([OH:24])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH2:20][CH:21]1[CH2:23][CH2:22]1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[CH:21]1([CH2:20][O:19][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[O:12][CH2:11][C@@H:10]([OH:24])[CH2:9][OH:8])[CH2:23][CH2:22]1

Participants

5

Reactant 2

HCID 13755497HCID 13755497, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13755499HCID 13755499, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (S)-1-benzyloxy-3-[o-(cyclopropylmethoxy)phenoxy]-2-hydroxypropane (10.97 g) in 100 ml ethanol, to which is added 3.5 g of 10% palladium on carbon, is hydrogenated at 45 lbs. pressure at room temperature until the uptake of hydrogen ceases (about 10 minutes). The catalyst is filtered off, washed with ethanol and the filtrate concentrated under reduced pressure leaving a crystalline residue that is recrystallized from 35 ml of ethanol; (S)-3-[o-(cyclopropylmethoxy)phenoxy]-1,2-propanediol, m.p. 95°-97°, [α]D25 =5.32° (c=0.99, CH3OH) is obtained.

Workup

  1. customat room temperature
  2. filtrationThe catalyst is filtered off
  3. washwashed with ethanol
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customleaving a crystalline residue that
  6. customis recrystallized from 35 ml of ethanol

Sources & evidence

ORD record
ord-eecb3dbd25134b8f9ce777247bc65e82
Source dataset
uspto-grants-1987_01
Patent number
US04634713

Reaction notes

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