Hydrochloric Acid → Ethyl (4-hydroxy-2-methylphenoxy)acetate

HRID 9625

Reaction equation

[CH2:1]([O:3][C:4](=[O:18])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13]C(=O)C)=[CH:9][C:8]=1[CH3:17])[CH3:2].[O-]CC.[Na+].Cl>C(O)C>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[CH3:17])[CH3:2]

Participants

Conditions

Temperature: 45 °C

Procedure

A solution of ethyl[4-(acetyloxy)-2-methylphenoxy]acetate (intermediate 6, 148 g) in ethanol (1300 ml) was treated with sodium ethoxide (41.3 g) and the mixture heated to 45° C. for 2.5 hours. The mixture as cooled to 22° C. and concentrated hydrochloric acid added to give a neutral (pH 7) solution. The resulting mixture was concentrated and the residue dissolved in a mixture of t-butylmethyl ether, water and brine. The organic layer was separated, washed with brine and dried over sodium sulfate and filtered. The filtrate was concentrated to give a brown solid which was further purified by precipitation from a solution in dichloromethane (100 ml) on addition of cyclohexane (710 ml) to give the title compound as a brown solid.

Workup

temperatureThe mixture as cooled to 22° C.

Sources & evidence

ORD record: ord-55f2e447a6be46f59025fb20b44ca092
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091237B2

Linked notes

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