Benzyl Bromide → Benzyl (1R,2S)-2-(4-hydroxyphenyl)cyclopropane carboxylate

HRID 922238Notes

Reaction equation

HRID 922238 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:10][C@H:9]2[C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.C(=O)(O)[O-].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:10][C@H:9]2[C:11]([O:13][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:12])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 516893Potassium BicarbonateHCID 86695754(1R,2S)-2-(4-Hydroxyphenyl)cyclopropanecarboxylic acid

Product 1

HCID 86695755Benzyl (1R,2S)-2-(4-hydroxyphenyl)cyclopropane carboxylateYield 58.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

To a 100 mL RB flask fitted with magnetic stirrer was charged with 50 mL of acetone. To the stirred solvent was added (1R,2S)-2-(4-hydroxyphenyl)cyclopropanecarboxylic acid (0.51 g, 2.86 mmol). The reaction mixture was brought to 0° C., potassium bicarbonate (0.28 g, 2.8 mmol), stirred for 10 minutes, benzyl bromide (0.3 mL, 2.8 mmol) was added drop wise. The reaction mixture was heated at 40° C. for 2 h. The reaction mixture was concentrated to distill off the solvent; water (25 mL) was added and extracted with ethyl acetate (25 mL). The organic layer was washed with brine solution (25 mL). The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as pale yellow liquid (0.44 g, yield: 57.2%). 1H NMR (300 MHz, CDCl3): δ 7.30 (s, 4H), 7.19 (s, 1H), 6.89-6.92 (d, 2H), 6.66-6.68 (d, 2H), 5.08 (s, 2H), 4.89 (s, 1H), 2.41-2.48 (m, 1H), 1.78-1.84 (m, 1H), 1.49-1.56 (m, 1H), 1.17-1.24 (m, 1H).

Workup

  1. customTo a 100 mL RB flask fitted with magnetic stirrer
  2. customwas brought to 0° C.
  3. concentrationThe reaction mixture was concentrated
  4. distillationto distill off the solvent
  5. additionwater (25 mL) was added
  6. extractionextracted with ethyl acetate (25 mL)
  7. washThe organic layer was washed with brine solution (25 mL)
  8. dry with materialThe organic layer was dried over Na2SO4
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9bbee9c096274647bdc8425aeb516ea3
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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