Pyridine → HCID 22134802, compound

HRID 908052Notes

Reaction equation

HRID 908052 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].N1C=CC=CC=1.[C:17](OC(=O)C)(=[O:19])[CH3:18]>ClCCl>[C:17]([O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[Cl:1])(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 170223-Chloro-4-hydroxybenzaldehyde

Product 1

HCID 22134802HCID 22134802, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To 3-chloro-4-hydroxybenzaldehyde (5.00 g, 31.9 mmol) and pyridine (5.0 mL, 61.8 mmol) in dichloromethane (40 mL) at 0° C. was added acetic anhydride (4.0 mL, 42.3 mmol) over a 20-minute period. The mixture was stirred for 1.5 hours more, warmed to 20° C., then worked up (10% hydrochloric acid wash) to afford 4-acetoxy-3-chlorobenzaldehyde as a pale-yellow solid (6.01 g, 92% yield): m.p. 33-35° C.; Rf0.30 (20% ethyl acetate/hexane); 1H NMR spectrum (400 MHz, CDCl3) δ 2.39 (s, 3, CH3), 7.34 (d, J=8.0 Hz, 1, ArH), 7.82 (dd, J=7.6,2 Hz, 1, ArH), 7.98 (d, J=1.6 Hz, 1, ArH), 9.96 ppm (s, 1, CHO).

Workup

  1. wash(10% hydrochloric acid wash)

Sources & evidence

ORD record
ord-bb892f36cb814a35a593f2d9adf45366
Source dataset
uspto-grants-2011_09
Patent number
USRE042700E1

Reaction notes

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