Acetic Anhydride → HCID 10199432, compound

HRID 1954262Notes

Reaction equation

HRID 1954262 reaction equation
[CH3:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]3[C:13](=[C:14]([C:15]4[CH:20]=[C:19]([CH3:21])[C:18]([OH:22])=[C:17]([CH3:23])[CH:16]=4)[C:4]=2[C:3]=1[CH3:24])[CH:12]=[CH:11][CH:10]=[CH:9]3.[C:25](OC(=O)C)(=[O:27])[CH3:26]>N1C=CC=CC=1>[CH3:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]3[C:13](=[C:14]([C:15]4[CH:20]=[C:19]([CH3:21])[C:18]([O:22][C:25](=[O:27])[CH3:26])=[C:17]([CH3:23])[CH:16]=4)[C:4]=2[C:3]=1[CH3:24])[CH:12]=[CH:11][CH:10]=[CH:9]3

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 18430701HCID 18430701, compound

Product 1

HCID 10199432HCID 10199432, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2,6-dimethyl-phenol (24.0 g, 72.2 mmol) in pyridine (200 mL) at 0° C. under nitrogen was added dropwise acetic anhydride (8.9 mL, 93.9 mmol) over a period of 10 min. After 45 min at 0° C., the reaction mixture was placed in the freezer for 18 h, then removed and stirred for 2 h in an ice bath that was allowed to warm to room temperature. The reaction mixture was poured onto water (1 L) and acidified with 10% hydrochloric acid to a pH of 1. The resulting mixture was extracted with diethyl ether (1 L), which was washed with 10% hydrochloric acid (1 L), twice with water (1 L), brine (700 mL), and dried (MgSO4). Concentration under reduced pressure and chromatography with petroleum ether:ethyl acetate (97:3) gave the title compound as a cream solid (22.4 g, 79%): NMR (CDCl3) δ 8.26 (s, 1 H), 7.87 (d, 1 H), 7.58 (d, 1 H), 7.44-7.40 (m, 1 H), 7.33-7.29 (m, 1 H), 7.07 (s, 2 H), 2.42 (s, 3 H), 2.41 (s, 3 H), 2.23 (s, 6 H), 1.67 (s, 3 H). MS(EI), [M+] 374. Anal. Calc. for C24H22O2S: C, 76.97, H, 5.92, N, 0.00. Found: C, 76.17, H, 5.75, N, 0.22.

Workup

  1. waitthe reaction mixture was placed in the freezer for 18 h
  2. customremoved
  3. additionThe reaction mixture was poured onto water (1 L)
  4. extractionThe resulting mixture was extracted with diethyl ether (1 L), which
  5. washwas washed with 10% hydrochloric acid (1 L), twice with water (1 L), brine (700 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationConcentration under reduced pressure and chromatography with petroleum ether:ethyl acetate (97:3)

Sources & evidence

ORD record
ord-5402da48e021437ea0024cee8ae99f56
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

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