Hydrochloric Acid → 3-Benzyloxy-4-hydroxyphenylacetic acid

HRID 5029Notes

Reaction equation

HRID 5029 reaction equation
C([O:3][C:4](=[O:21])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:7]=1)C.[OH-].[Na+].Cl>O>[CH2:14]([O:13][C:8]1[CH:7]=[C:6]([CH2:5][C:4]([OH:21])=[O:3])[CH:11]=[CH:10][C:9]=1[OH:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54479398Ethyl [3-(benzyloxy)-4-hydroxyphenyl]acetate

Product 1

HCID 197976433-Benzyloxy-4-hydroxyphenylacetic acidYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.35 g of the ester obtained above was added to a mixture of 50 ml of water and 1.49 g of sodium hydroxide. The resultant solution was refluxed for 2.5 hours, acidified with concentrated hydrochloric acid and evaporated under reduced pressure to give solids, which were purified by Soxhlet extraction apparatus to provide 4.27 g(yield 89%) of the desired compound as a yellow solid, having the characteristics of: m.p. 130°-133° C.; NMR(CDCl3, 200 MHz) δ3.45(s, 2H, CH2Ar), 5.09 (s, 2H, OCH2), 6.75-7.40(m, 6H, ArH).

Workup

  1. customevaporated under reduced pressure
  2. customto give solids, which
  3. customwere purified by Soxhlet extraction apparatus

Sources & evidence

ORD record
ord-b4cfc43b497244389389a726047b0d23
Source dataset
uspto-grants-1993_09
Patent number
US05242944

Reaction notes

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