Hydrochloric Acid → 1-(4-Benzyloxy-2,3-dimethyl-phenoxymethyl)-cyclopropanecarboxylic acid

HRID 2102991Notes

Reaction equation

C([O:3][C:4]([C:6]1([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:13]([CH3:25])[C:12]=2[CH3:26])[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+].O.Cl>CO>[CH2:18]([O:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][CH2:9][C:6]2([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]2)=[C:12]([CH3:26])[C:13]=1[CH3:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of the ester prepared as above (0.78 g) in MeOH (20 mL), was added NaOH solution (10% wt, 3 mL) and water (2 mL). After stirring the solution at 50° C. for 4 h it was poured into water, and diluted HCl solution was added to adjust pH to 3. The mixture was partitioned between EtOAc and water, and the organic layer was washed with water, dried over MgSO4 and evaporated. The residue was purified by silica gel column eluting with 40% EtOAc in hexane to give 0.6 g of 1-(4-benzyloxy-2,3-dimethyl-phenoxymethyl)-cyclopropanecarboxylic acid as a pale solid.

Workup

additionwas added
customThe mixture was partitioned between EtOAc and water
washthe organic layer was washed with water
dry with materialdried over MgSO4
customevaporated
customThe residue was purified by silica gel column
washeluting with 40% EtOAc in hexane

Sources & evidence

ORD record: ord-be34c227fc104e628df7abee84d83988
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576094B2

Reaction notes

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