Water → Benzyl 5-(benzyloxy)-2-methylbenzoate

HRID 1914245Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C=O)C.CC(=O)OCC>[CH2:18]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH2:11][C:5]1[CH:6]=[CH:10][CH:2]=[CH:3][CH:4]=1)=[O:8])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2.6 g of 5-hydroxy-2-methylbenzoic acid (see below), 7.0 g potassium carbonate and 3.8 ml benzyl chloride in 50 ml DMF are stirred at 50° C. for two hours, until the reaction is completed according to TLC analysis. The reaction mixture is portioned between water and EA, and the phases are separated. The organic phase is washed three times with 1 M sodium carbonate solution and once with brine, dried over MgSO4, and the solvent is removed under reduced pressure yielding benzyl 5-(benzyloxy)-2-methylbenzoate, which is used for the next step without further purification.

Workup

customthe phases are separated
washThe organic phase is washed three times with 1 M sodium carbonate solution
dry with materialonce with brine, dried over MgSO4
customthe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-b0065446578344e28eb4efffbc1b1996
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609848B2

Reaction notes

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