4-Toluenesulfonyl chloride → HCID 86599068, compound

HRID 2115920Notes

Reaction equation

HRID 2115920 reaction equation
C(C1C(C)=C(Cl)C=C(C(C)C)C=1O)C=C.ClC1C=C(C=CC=1)C(OO)=O.C(=O)([O-])[O-].[K+].[K+].[Cl:33][C:34]1[CH:35]=[C:36]([CH:46]([CH3:48])[CH3:47])[C:37]2[O:41][CH:40]([CH2:42][OH:43])[CH2:39][C:38]=2[C:44]=1[CH3:45].[C:49]1([CH3:59])[CH:54]=[CH:53][C:52]([S:55](Cl)(=[O:57])=[O:56])=[CH:51][CH:50]=1>>[CH3:59][C:49]1[CH:54]=[CH:53][C:52]([S:55]([O:43][CH2:42][CH:40]2[CH2:39][C:38]3[C:44]([CH3:45])=[C:34]([Cl:33])[CH:35]=[C:36]([CH:46]([CH3:48])[CH3:47])[C:37]=3[O:41]2)(=[O:57])=[O:56])=[CH:51][CH:50]=1

Participants

6

Reactant 5

HCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 68966163HCID 68966163, compound2×HCID 86599067HCID 86599067, compound

Product 1

HCID 86599068HCID 86599068, compoundYield 69%

Procedure

Treatment of 2-allyl-4-chloro-6-isopropyl-3-methylphenol (8.88 g, 0.04 mmol) with 3-chloroperoxybenzoic acid (13.63 g, 0.079 mol, 77%)) followed by potassium carbonate (10.92 g, 0.079 mol) generally according to the procedure described for Intermediate 9 provided (±)-(5-chloro-7-isopropyl-4-methyl-2,3-dihydro-1-benzofuran-2-yl)methanol. Treatment of (±)-(5-chloro-7-isopropyl-4-methyl-2,3-dihydro-1-benzofuran-2-yl)methanol (5.95 g, 0.025 mol) with p-toluenesulfonyl chloride (5.66 g, 0.03 mol) generally according to the procedure described for Intermediate 10 afforded 6.71 g (69%) (±)-(5-chloro-7-isopropyl-4-methyl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate as a white solid. mp 103-105° C.; Anal. calcd. for C20H23ClO4S C, 60.83; H, 5.87. Found C, 60.67; H, 5.88.

Sources & evidence

ORD record
ord-378f36bf510644989dd51256b7b35401
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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