Acetyl chloride → (4-(6-Acetyloxy-1-benzothiophen-2-yl)phenyl) acetate

HRID 1870267Notes

Reaction equation

HRID 1870267 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3[CH:13]=[C:14]([OH:17])[CH:15]=[CH:16][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:25](Cl)(=[O:27])[CH3:26].[O:29]1CC[CH2:31][CH2:30]1>>[C:25]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3[CH:13]=[C:14]([O:17][C:30](=[O:29])[CH3:31])[CH:15]=[CH:16][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1)(=[O:27])[CH3:26]

Participants

5

Reactant 4

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 4459202-(4-Hydroxyphenyl)benzo(b)thiophen-6-ol

Product 1

HCID 9905410(4-(6-Acetyloxy-1-benzothiophen-2-yl)phenyl) acetate

Procedure

2-(4-Hydroxyphenyl)-6-hydroxybenzo[b]thiophene (2.42 g, 10 mmol) was dissolved in 100 mL of tetrahydrofuran and triethylamine (8 g, 100 mmol) was added. The reaction mixture was stirred under a nitrogen atmosphere at ambient temperature, while acetylchloride (2 g, 30 mmol) was slowly added. After sixteen hours, the reaction was terminated by the addition of water. The product began to crystallize at the interface, the water layer was discarded, and product crystallized out of the tetrahydrofuran layer. The product was filtered off and dried to give 2.06 of the title compound. 1H NMR: (d6 -DMSO)δ 7.86 (s, 1H) 7.85 (d, 1H), 7.83 (s, 1H), 7.81 (d, 1H), 8.70 (d, 2H), 7.25 (d, 2H), 7.18 (dd, 1H). EA calculated for C18H14O4S: C, 66.24; H, 4.32 Found: C, 66.14; H, 4.38. MS(FD): m/e=326 (M+).

Workup

  1. additionwas slowly added
  2. waitAfter sixteen hours
  3. customthe reaction was terminated by the addition of water
  4. customto crystallize at the interface
  5. customproduct crystallized out of the tetrahydrofuran layer
  6. filtrationThe product was filtered off
  7. customdried

Sources & evidence

ORD record
ord-68c3c9ad4c4b43e1b1eb07b3fafe0ef2
Source dataset
uspto-grants-2000_08
Patent number
US06096781

Reaction notes

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