Water → Bis(2-methylphenyl)methanone

HRID 895772Notes

Reaction equation

HRID 895772 reaction equation
S1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2N=C1.[Li][CH2:11][CH2:12][CH2:13][CH3:14].[C:15](OCC)(=O)C.O.[CH2:22]1[CH2:26][O:25][CH2:24][CH2:23]1>>[C:13]1([CH3:14])[C:23]([C:24]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[CH3:15])=[O:25])=[CH:22][CH:26]=[CH:11][CH:12]=1

Participants

6

Reactant 5

HCID 962WaterHCID 7222BenzothiazoleHCID 8028Tetrahydrofuran2×HCID 8857Ethyl AcetateHCID 178418339Butyllithium

Product 1

HCID 219387Bis(2-methylphenyl)methanoneYield 64%

Conditions

Temperature
25 °C

Procedure

Step 5 Under anhydrous conditions the benzothiazole acid (step 4) was dissolved in THF (0.052 M). At −78° C. added BuLi (2.2 eq). After 1 h at −78° C. to 0° C., added the amide (1.28 eq) from step 1 of Example 81, in THF, at −78° C., over 5 min. After 0.5 h at −78° C., the reaction was allowed to warm to 25° C. After stirring at 25° C. for 2 h, workup with ethyl acetate and water and chromatography afforded pure tolyl ketone acid product (64%).

Workup

  1. waitAfter 0.5 h at −78° C.

Sources & evidence

ORD record
ord-5399eb0d3fe44e1399b865a426fdc97c
Source dataset
uspto-grants-2005_07
Patent number
US06916841B2

Reaction notes

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