P-Cresol → Ethyl 2-(4-methylphenoxy)phenylacetate

HRID 1492301Notes

Reaction equation

HRID 1492301 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.[H-].[Na+].[H][H].[CH2:13]([O:15][C:16](=[O:25])[CH:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)Br)[CH3:14]>CN(C)C=O.O>[CH3:8][C:3]1[CH:4]=[CH:5][C:6]([O:7][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH2:17][C:16]([O:15][CH2:13][CH3:14])=[O:25])=[CH:1][CH:2]=1

Participants

7

Reactant 4

HCID 2879P-CresolHCID 24758Sodium hydrideHCID 97780Ethyl bromophenylacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 18952394Ethyl 2-(4-methylphenoxy)phenylacetateYield 60.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

p-Cresol (4.45 g) was added portionwise over 30 minutes to a stirred suspension of sodium hydride (60% dispersion in mineral oil; 1.81 g) in N,N-dimethylformamide (DMF) (80 ml). When evolution of hydrogen ceased, ethyl-α-bromophenylacetate (10.0 g) was added and the mixture was left to stand for 20 hours. Water (500 ml) was added and the mixture was extracted with ethyl acetate (2×250 ml). The extracts were washed with water (250 ml), followed by saturated sodium chloride solution (250 ml) and then dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by flash chromatography, eluting with ethyl acetate/hexane (1:19 v/v), to give ethyl 2-(4-methylphenoxy)phenylacetate (B) (6.7 g), as an oil; NMR (d6 -DMSO): 1.2(t, 3H), 2.15(s, 3H), 4.1(q, 2H), 5.9(s, 1H), 7.2-7.6(m, 9H).

Workup

  1. waitthe mixture was left
  2. extractionthe mixture was extracted with ethyl acetate (2×250 ml)
  3. washThe extracts were washed with water (250 ml)
  4. dry with materialdried (MgSO4)
  5. customVolatile material was removed by evaporation
  6. customthe residue was purified by flash chromatography
  7. washeluting with ethyl acetate/hexane (1:19 v/v)

Sources & evidence

ORD record
ord-086030faa0bf44238292e04fd9d72f14
Source dataset
uspto-grants-1994_12
Patent number
US05373015

Reaction notes

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