Hydroxyphenylacetic acid → Benzyl 2-(4-hydroxyphenyl)acetate

HRID 1290521Notes

Reaction equation

HRID 1290521 reaction equation
[H-].[Na+].[CH3:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=[O:18])=[CH:12][CH:11]=1.[CH3:20]N(C=O)C>>[OH:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][C:17]([O:19][CH2:20][C:5]2[CH:4]=[CH:3][CH:8]=[CH:7][CH:6]=2)=[O:18])=[CH:14][CH:15]=1

Participants

5

Reactant 4

HCID 127Hydroxyphenylacetic acidHCID 6228DimethylformamideHCID 8058HexaneHCID 24758Sodium hydride

Product 1

HCID 11107524Benzyl 2-(4-hydroxyphenyl)acetate

Conditions

Temperature
4 °C

Procedure

Sodium hydride (50% w/w dispersion in mineral oil, 3.7 g) was treated under argon with repeated washes of hexane. The oil-free residue was suspended in dry DMF (100 ml) and 4-hydroxyphenylacetic acid (13.0 g) was added portionwise to the stirred cooled (4° C.) mixture. After 30 minutes, benzyl bormide (9.2 ml) was added dropwise and, after a further 1 hour at 4° C., stirring was continued overnight at ambient temperature. The solvent was evaporated in vacuo and the residue partitioned between ethyl acetate and water. The aqueous phase was re-extracted with further ethyl acetate and the combined organic extracts washed with water and brine, then dried (MgSO4) and evaporated. The crystaline residue gave benzyl 4-hydroxyphenylacetate, 17.8 g, as off-white crystals: m.p. 70°-72° C. NMR (CDCl3) δ7.32(5H,m), 7.14(2H,d), 6.76(2H,d), 5.12(2H,s), 3.59(2H,s); m/e 242 (M·)+.

Workup

  1. additionbenzyl bormide (9.2 ml) was added dropwise and, after a further 1 hour at 4° C.
  2. waitwas continued overnight at ambient temperature
  3. customThe solvent was evaporated in vacuo
  4. customthe residue partitioned between ethyl acetate and water
  5. extractionThe aqueous phase was re-extracted with further ethyl acetate
  6. washthe combined organic extracts washed with water and brine
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-82648b5e27604dd6b28a52b9d2e4e2de
Source dataset
uspto-grants-1998_05
Patent number
US05750754

Reaction notes

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