4-Toluenesulfonyl chloride → HCID 19749590, compound

HRID 2115917Notes

Reaction equation

HRID 2115917 reaction equation
C(C1C=CC=C(C(C)C)C=1O)C=C.ClC1C=C(C=CC=1)C(OO)=O.C(=O)([O-])[O-].[K+].[K+].[CH:31]([C:34]1[C:42]2[O:41][CH:40]([CH2:43][OH:44])[CH2:39][C:38]=2[CH:37]=[CH:36][CH:35]=1)([CH3:33])[CH3:32].[C:45]1([CH3:55])[CH:50]=[CH:49][C:48]([S:51](Cl)(=[O:53])=[O:52])=[CH:47][CH:46]=1>>[CH3:55][C:45]1[CH:50]=[CH:49][C:48]([S:51]([O:44][CH2:43][CH:40]2[CH2:39][C:38]3[CH:37]=[CH:36][CH:35]=[C:34]([CH:31]([CH3:33])[CH3:32])[C:42]=3[O:41]2)(=[O:53])=[O:52])=[CH:47][CH:46]=1

Participants

6

Reactant 5

HCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 12667321HCID 12667321, compoundHCID 68961080HCID 68961080, compound2×

Product 1

HCID 19749590HCID 19749590, compoundYield 79%

Procedure

Treatment of 2-allyl-6-isopropylphenol (8.81 g, 0.05 mmol) with 3-chloroperoxybenzoic acid (22.43 g, 0.13 mol, 77%)) followed by potassium carbonate (13.82 g, 0.1 mol) generally according to the procedure described for Intermediate 9 provided (±)-(7-isopropyl-2,3-dihydro-1-benzofuran-2-yl)methanol. Treatment of (±)-(7-isopropyl-2,3-dihydro-1-benzofuran-2-yl)methanol (3.45 g, 0.018 mol) with p-toluenesulfonyl chloride (3.92 g, 0.021 mol) generally according to the procedure described for Intermediate 10 afforded 4.91 g (79%) (±)-(7-isopropyl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate as a colorless oil. Anal. calcd. for C19H22O4S C, 65.87; H, 6.4. Found C, 65.63; H, 6.32.

Sources & evidence

ORD record
ord-92a3c2433ca449f6b499397564601eca
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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