Hydroxyphenylacetic acid → HCID 19748801, compound

HRID 484051Notes

Reaction equation

HRID 484051 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:14]([O:16][CH:17]([O:20][CH2:21][CH3:22])[CH2:18]Br)[CH3:15].Cl>CS(C)=O.CCOCC>[CH2:14]([O:16][CH:17]([O:20][CH2:21][CH3:22])[CH2:18][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1)[CH3:15]

Participants

7

Reactant 4

HCID 127Hydroxyphenylacetic acidHCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 19748801HCID 19748801, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4-hydroxyphenylacetic acid (50.0 gm, 0.33 mol) in DMSO (300 mL) was added 50% aqueous NaOH (57.0 gm, 0.71 mol) with stirring. After stirring for 10 min at room temperature bromoacetaldehyde diethyl acetal (66.0 gm, 0.33 mol) was added. The solution was heated at 100°-110° C. for 2 hr when an additional 2 gm of 50% NaOH was added. After heating for another hour the reaction mixture was cooled and poured into a mixture of aqueous HCl (30 mL of conc. HCl in 400 mL ice-H2O) and Et2O. The layers were separated and hexane was added to the Et2O layer. The organic layer was washed successively with H2O (twice) and saturated NaCl before being dried over Na2SO4, filtered and evaporated to dryness to give 83.7 gm (0.31 mol) of 4-[(2,2-diethoxy)ethoxy]phenylacetic acid which was suitable for use in the next step.

Workup

  1. additionwas added
  2. additionwas added
  3. temperatureAfter heating for another hour the reaction mixture
  4. temperaturewas cooled
  5. customThe layers were separated
  6. additionhexane was added to the Et2O layer
  7. washThe organic layer was washed successively with H2O (twice) and saturated NaCl
  8. dry with materialbefore being dried over Na2SO4
  9. filtrationfiltered
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-80284cc62f9d4c149aee653b752e78d8
Source dataset
uspto-grants-1993_07
Patent number
US05229381

Reaction notes

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