Hydrochloric Acid → 2-(4-(Benzyloxy)phenyl)-2-hydroxyacetic acid

HRID 2380389Notes

Reaction equation

HRID 2380389 reaction equation
O.[OH:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]([OH:11])[C:8]([O-:10])=[O:9])=[CH:5][CH:4]=1.[Na+].[OH-].[Na+].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>O>[CH2:17]([O:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]([OH:11])[C:8]([OH:10])=[O:9])=[CH:5][CH:4]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 14798Sodium Hydroxide2×HCID 236981332-Hydroxy-2-(4-hydroxyphenyl)acetic acid, sodium salt hydrate

Product 1

HCID 140103192-(4-(Benzyloxy)phenyl)-2-hydroxyacetic acidYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 41.6 g (0.20 mol) of sodium 4-hydroxymandelate monohydrate, 9.6 g (0.24 mol) of sodium hydroxide and 27.9 g (0.22 mol) of benzyl chloride in 50 ml of water is stirred at 70° C. for 17 hours. The mixture is then diluted with 50 ml of water, and another 4.0 g (0.10 mol) of sodium hydroxide are added. The reaction mixture is refluxed for one hour, then cooled, acidified with concentrated hydrochloric acid, and the precipitated product is filtered. The residue is washed with cold water and then dried in a high vacuum, giving 35.6 g (69%) of 4-benzyloxymandelic acid, melting point 148°-155° C.

Workup

  1. temperatureThe reaction mixture is refluxed for one hour
  2. temperaturecooled
  3. filtrationthe precipitated product is filtered
  4. washThe residue is washed with cold water
  5. customdried in a high vacuum

Sources & evidence

ORD record
ord-f9941176b72b41f3a3811870904eb6eb
Source dataset
uspto-grants-1994_11
Patent number
US05367008

Reaction notes

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