Hydroxyphenylacetic acid → Tert-butyl 2-(4-hydroxyphenyl)acetate

HRID 484045Notes

Reaction equation

HRID 484045 reaction equation
OS(O)(=O)=O.[OH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1.[CH3:17][C:18](=[CH2:20])[CH3:19].C([O-])(O)=O.[Na+]>O1CCOCC1>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][C:14]([O:16][C:18]([CH3:20])([CH3:19])[CH3:17])=[O:15])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 127Hydroxyphenylacetic acidHCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 516892Sodium Bicarbonate

Product 1

HCID 15932404Tert-butyl 2-(4-hydroxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of H2SO4 (5 ml) in dioxane (80 ml) was added to 4-hydroxyphenylacetic acid (20 gm, 0.13 mol) in a pressure bottle. Isobutylene (250 ml) was added and the bottle was sealed and the mixture was stirred for 24 hr. The reaction mixture was poured into saturated NaHCO3 solution and extracted with EtOAc. The combined organic extracts were washed successively with saturated NaHCO3, H2O (twice) and brine before being dried over Na2SO4 and evaporated to dryness. Crystals formed after standing overnight and they were filtered, washed with cold hexane and dried to give 20.99 gm of the title compound. M.pt. 95°-96° C.

Workup

  1. customthe bottle was sealed
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed successively with saturated NaHCO3, H2O (twice) and brine
  4. dry with materialbefore being dried over Na2SO4
  5. customevaporated to dryness
  6. customCrystals formed
  7. waitafter standing overnight
  8. filtrationthey were filtered
  9. washwashed with cold hexane
  10. customdried

Sources & evidence

ORD record
ord-eccc3a4ff480432f8bdb32903b64b671
Source dataset
uspto-grants-1993_07
Patent number
US05229381

Reaction notes

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