4-Toluenesulfonyl chloride → HCID 86599072, compound

HRID 2115927Notes

Reaction equation

HRID 2115927 reaction equation
C(C1C=C(Cl)C=C(C(C)(C)C)C=1O)C=C.ClC1C=C(C=CC=1)C(OO)=O.C(=O)([O-])[O-].[K+].[K+].[C:33]([C:37]1[C:45]2[O:44][CH:43]([CH2:46][OH:47])[CH2:42][C:41]=2[CH:40]=[C:39]([Cl:48])[CH:38]=1)([CH3:36])([CH3:35])[CH3:34].[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:47][CH2:46][CH:43]2[CH2:42][C:41]3[CH:40]=[C:39]([Cl:48])[CH:38]=[C:37]([C:33]([CH3:36])([CH3:34])[CH3:35])[C:45]=3[O:44]2)(=[O:57])=[O:56])=[CH:51][CH:50]=1

Participants

6

Reactant 5

HCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 68966425HCID 68966425, compoundHCID 86599071HCID 86599071, compound

Product 1

HCID 86599072HCID 86599072, compoundYield 51%

Procedure

Treatment of 2-tert-butyl-4-chlorophenol (12.73 g, 0.070 mol) with allyl bromide (10.01 g, 0.083 mol) and potassium carbonate (38.11 g, 0.276 mol) followed by refluxing the resultant allyl ether in mesitylene generally according to the procedure described for Intermediate 8 gave 2-allyl-6-tert-butyl-4-chlorophenol. Treatment of the phenol with 3-chloroperoxybenzoic acid (35.90 g, 0.146 mol, 77%) followed by potassium carbonate (28.18 g, 0.204 mol) generally according to the procedure described for Intermediate 9 provided (±)-(7-tert-butyl-5-chloro-2,3-dihydro-1-benzofuran-2-yl)methanol. Treatment of the alcohol with with p-toluenesulfonyl chloride (10.27 g, 0.054 mol) generally according to the procedure described for Intermediate 10 afforded 13.84 g (51%) (±)-(7-tert-butyl-5-chloro-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate as a white solid. mp 74-77° C.; Anal. calcd. for C20H23ClO4S C, 60.83; H, 5.87. Found C, 60.79; H, 5.80.

Sources & evidence

ORD record
ord-aa3379ba7cf4475c92e54823f9950871
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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