3,5-Dimethylphenol → HCID 22479338, compound

HRID 1593233Notes

Reaction equation

[CH3:1][C:2]([CH3:19])([CH2:7]OS(C1C=CC(C)=CC=1)(=O)=O)[C:3]([O:5][CH3:6])=[O:4].C[C:21]1[CH:22]=[C:23]([OH:28])[CH:24]=[C:25]([CH3:27])[CH:26]=1.[C:29](=O)([O-])[O-].[K+].[K+].CC(N(C)C)=O>O>[CH3:27][C:25]1[CH:24]=[C:23]([O:28][CH2:1][C:2]([CH3:19])([CH3:7])[C:3]([O:5][CH3:6])=[O:4])[CH:22]=[CH:21][C:26]=1[CH3:29]

Participants

Conditions

Temperature: 170 °C

Procedure

A reaction vessel was charged with methyl 2,2-dimethyl-3-tosyloxypropionate (Intermediate A7, 100 g, 0.35 mol), 3,5-dimethylphenol (45 g, 0.37 mol), potassium carbonate (73 g, 0.53 mol), and dimethylacetamide (300 mL). The mixture was heated on a steam bath for 16 hr and in a 170° C. bath for 6 hr. The cooled reaction mixture was diluted with 1 L water and extracted with 2×200 mL portions of ethyl acetate. The combined organic layers were washed with water, 0.5 M sodium hydroxide (twice), water, and saturated aqueous sodium chloride. The solvent was removed at aspirator pressure and high vacuum. The residue was taken up in dichloromethane and washed with several portions of 1 M sodium hydroxide, water, and saturated sodium chloride. The solution was concentrated, and the residue was distilled at 2 torr to yield 43.5 g (52%) of the title compound.

Workup

customThe cooled reaction mixture
extractionextracted with 2×200 mL portions of ethyl acetate
washThe combined organic layers were washed with water, 0.5 M sodium hydroxide (twice), water, and saturated aqueous sodium chloride
customThe solvent was removed at aspirator pressure and high vacuum
washwashed with several portions of 1 M sodium hydroxide, water, and saturated sodium chloride
concentrationThe solution was concentrated
distillationthe residue was distilled at 2 torr

Sources & evidence

ORD record: ord-8c36edc5ee3442d484c478ec421ef18e
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07294716B2

Reaction notes

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