Water → 3-(4-Hydroxyphenyl)hex-4-ynoic acid

HRID 2070544Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:12]2C(=O)OC(C)(C)[O:14][C:13]2=[O:21])[C:9]#[C:10][CH3:11])=[CH:4][CH:3]=1.O.[Cl-].[Na+]>CCC(=O)CC>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:9]#[C:10][CH3:11])[CH2:12][C:13]([OH:21])=[O:14])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of 5-[1-(4-hydroxyphenyl)-but-2-ynyl]-2,2-dimethyl-[1,3]dioxan e-4,6-dione (54.8 g) obtained in Substep 2 in 3-pentanone (200 mL) was added water (100 mL), followed by stirring the reaction mixture at 100° C. for 2 days. After cooling down to room temperature, the aqueous layer of the reaction mixture was saturated with sodium chloride, followed by extraction with 3-pentanone. The organic layer was dried and concentrated, followed by recrystallizing the residue from an ethyl acetate-hexane mixed solvent to give 3-(4-hydroxyphenyl)-hex-4-ynoic acid (34.2 g).

Workup

temperatureAfter cooling down to room temperature
extractionfollowed by extraction with 3-pentanone
customThe organic layer was dried
concentrationconcentrated
customby recrystallizing the residue from an ethyl acetate-hexane mixed solvent

Sources & evidence

ORD record: ord-d064c8afb20540b7b527534906499911
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299296B2

Reaction notes

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