Acetic Anhydride → HCID 18984733, compound

HRID 1439916Notes

Reaction equation

HRID 1439916 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([CH2:9][CH2:10][CH2:11][OH:12])[CH:3]=1.C(N(CC)CC)C.[C:20](OC(=O)C)(=[O:22])[CH3:21]>CN(C)C1C=CN=CC=1.ClCCl.O>[C:20]([O:12][CH2:11][CH2:10][CH2:9][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[CH3:8])(=[O:22])[CH3:21]

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 18984718HCID 18984718, compound

Product 1

HCID 18984733HCID 18984733, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-chloro-2-(3-hydroxypropyl)toluene (3.7 g, 20 mmol), triethylamine (40 mmol) and 4-dimethylaminopyridine (4 mmol) in dichloromethane (20 mL) was added acetic anhydride (15 mmol) at 0° C. The mixture was stirred for ca. 1 h at 0° C., diluted with water, and extracted with AcOEt. The extract was washed with diluted aqueous HCl and brine, dried over MgSO4, and concentrated to give quantitatively the title compound: 1H NMR (CDCl3) δ7.11 (bs, 1H), 7.07 (bs, 2H), 4.07 (t, 2H, J=7.2 Hz), 2.65 (dd, 2H, J=7.2, 8.1 Hz), 2.28 (s, 3H), 2.05 (s, 3H), 1.84~1.96 (m, 2H). 5) 2-(3-Acethoxypropyl)-4-chloro-6-nitrotoluene

Workup

  1. extractionextracted with AcOEt
  2. washThe extract was washed with diluted aqueous HCl and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-370a8440d058409d962537bda3bcba82
Source dataset
uspto-grants-1996_03
Patent number
US05496843

Reaction notes

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