4-(Chlorosulfonyl)-2-hydroxybenzoic acid → 4-[4-(2-Benzyl-4,5-dimethyl-furan-3-carbonyl)-2,6-diisopropyl-phenoxysulfonyl]-2-hydroxy-benzoic acid

HRID 1871287Notes

Reaction equation

HRID 1871287 reaction equation
[CH2:1]([C:8]1[O:9][C:10]([CH3:29])=[C:11]([CH3:28])[C:12]=1[C:13]([C:15]1[CH:20]=[C:19]([CH:21]([CH3:23])[CH3:22])[C:18]([OH:24])=[C:17]([CH:25]([CH3:27])[CH3:26])[CH:16]=1)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[S:31]([C:34]1[CH:42]=[CH:41][C:37]([C:38]([OH:40])=[O:39])=[C:36]([OH:43])[CH:35]=1)(=[O:33])=[O:32]>>[CH2:1]([C:8]1[O:9][C:10]([CH3:29])=[C:11]([CH3:28])[C:12]=1[C:13]([C:15]1[CH:16]=[C:17]([CH:25]([CH3:27])[CH3:26])[C:18]([O:24][S:31]([C:34]2[CH:42]=[CH:41][C:37]([C:38]([OH:40])=[O:39])=[C:36]([OH:43])[CH:35]=2)(=[O:33])=[O:32])=[C:19]([CH:21]([CH3:22])[CH3:23])[CH:20]=1)=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 146685314-(Chlorosulfonyl)-2-hydroxybenzoic acidHCID 15895033(2-Benzyl-4,5-dimethyl-furan-3-yl)-(3,5-diisopropyl-4-hydroxy-phenyl)-methanone

Product 1

HCID 98299574-[4-(2-Benzyl-4,5-dimethyl-furan-3-carbonyl)-2,6-diisopropyl-phenoxysulfonyl]-2-hydroxy-benzoic acidYield 9%

Procedure

The title compound was prepared according to the procedure in Example 4 using (2-benzyl-4,5-dimethyl-furan-3-yl)-(3,5-diisopropyl-4-hydroxy-phenyl)-methanone (0.300 g, 0.768 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (0.218 g, 0.922 mmol) to give 0.04 g (9%) of the title compound as a tan solid, mp 142-143° C.; 1H NMR (DMSO-d6) δ 1.04 (d, 12 H), 1.81 (s, 3 H), 2.19 (s, 3 H), 3.07 (septet, 2 H), 3.81 (s, 2 H), 6.95-6.97 (m, 2 H), 7.14-7.20 (m, 3 H), 7.40-7.46 (m, 2 H), 7.47 (s, 2 H), 8.03 (d, 1 H). IR (KBr) 3400, 2950, 1675, 1375, 1180 cm-1. mass spectrum (EI), m/z 590 (M+). Anal. Calcd. for C33H34O8S.1.1H2O: C, 64.92; H, 5.98; N, 0.00. Found: C, 64.92; H, 5.76; N, -0.03.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-f89bdd178bda45a79b0f201bb5168067
Source dataset
uspto-grants-2000_08
Patent number
US06103708

Reaction notes

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