Water → Methyl 2-(2-(benzyloxy)phenyl)acetate

HRID 1608150Notes

Reaction equation

HRID 1608150 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C=O)C>[CH2:19]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 89719Methyl (2-hydroxyphenyl)acetate

Product 1

HCID 11076055Methyl 2-(2-(benzyloxy)phenyl)acetateYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Methyl 2-hydroxyphenylacetate (21.0 g) was dissolved in dry DMF (200 ml), and dry potassium carbonate (19.35 g) was added in one portion. Benzyl bromide (23.94 g) in dry DMF (50 ml) was added dropwise to this mixture, with stirring, at room temperature. After eighteen hours the mixture was poured into water (500 ml) and extracted with ether (2×400 ml). The extracts were washed with water (3×150 ml) and brine (100 ml), dried and filtered through silica gel (50 g; Merck 60), then concentrated under reduced pressure to afford a yellow oil. Distillation at 160° C. and 0.05 mmHg afforded methyl 2-benzyloxyphenylacetate as a clear, colourless oil (26.99 g; 83% yield), infrared maximum (film): 1730 cm-1 ; 1H nmr (CDCl3, 90 MHz): delta 3.60 (3H, s), 3.75 (2H, s), 4.10 (2H, s), 6.80-7.40 (9H, m) ppm.

Workup

  1. extractionextracted with ether (2×400 ml)
  2. washThe extracts were washed with water (3×150 ml) and brine (100 ml)
  3. customdried
  4. filtrationfiltered through silica gel (50 g; Merck 60)
  5. concentrationconcentrated under reduced pressure
  6. customto afford a yellow oil
  7. distillationDistillation at 160° C.

Sources & evidence

ORD record
ord-e455ec97d5ef404f9a3d0efc28735d9d
Source dataset
uspto-grants-1989_09
Patent number
US04870075

Reaction notes

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