Benzyl Bromide → Benzyl 2-benzyloxy-3-isopropylbenzoate

HRID 1739473Notes

Reaction equation

HRID 1739473 reaction equation
[OH:1][C:2]1[C:10]([CH:11]([CH3:13])[CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C([O-])([O-])=O.[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CC(C)=O>[CH2:20]([O:1][C:2]1[C:10]([CH:11]([CH3:13])[CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:4][C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:2]=1)=[O:5])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2018873-Isopropylsalicylic acid

Product 1

HCID 13791537Benzyl 2-benzyloxy-3-isopropylbenzoateYield 130.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2-hydroxy-3-isopropylbenzoic acid (5 g, 27.8 mmol) in acetone (40 ml) was treated with K2CO3 (7.67 g, 55.6 mmol) and benzyl bromide (9.98 g; 58.4 mmol). The reaction was stirred at ambient temperature for 60 hours, then evaporated. The residue was partitioned between ethyl acetate/H2O and the organic phase dried (MgSO4) and evaporated. The residue was purified by chromatography (eluant: ethyl acetate/hexane) to give benzyl 2-benzyloxy-3-isopropylbenzoate (6.52 g, 18.11 mmol, 65%)

Workup

  1. customevaporated
  2. customThe residue was partitioned between ethyl acetate/H2O
  3. dry with materialthe organic phase dried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by chromatography (eluant: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-de1b89f941074d7da99c0252f9a7763e
Source dataset
uspto-grants-1999_10
Patent number
US05965741

Reaction notes

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