Hydrochloric Acid → HCID 86639777, compound

HRID 2095216Notes

Reaction equation

HRID 2095216 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[CH:4]=[O:5].Cl.[P:12](Cl)([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])=[O:13]>ClCCl.C(N(CC)CC)C>[P:12]([O:1][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[CH:4]=[O:5])([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 13139Diethyl chlorophosphateHCID 69184Benzaldehyde, 2-hydroxy-5-methyl-

Product 1

HCID 86639777HCID 86639777, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2-hydroxy-5-methyl benzaldehyde (4A) (1000 mg) in dry dichloromethane (20 mL) and triethylamine (2 mL), diethyl chlorophosphate (1.17 mL) was added in a dropwise manner. The mixture was stirred for overnight and the reaction mixture was acidified using 5% HCl and extracted with ethyl acetate and the extracts were combined, washed with sodium bicarbonate and then concentrated. Flash column chromatography furnished the pure product as colorless oil (1620 mg, 81%): 1H-NMR (500 MHz, CDCl3) δ 10.34 (s, 1H), 7.7 (s, 1H), 7.3-7.4(d, J=8.4 Hz, 1H)7.3 (d, J=8.4 MHz), 4.2-4.3 (m, 4H) 2.3 (s, 3H), 1.3(t, J=6 Hz, 6H) (FIG. 7). 13C-NMR (CDCl3, 50.3 MHz) δ 188.5, 136.1, 135.1, 128.7, 120.8, 664.8, 20.4, 15.9. 31P-NMR (CDCl3, 81 MHz) δ −6.18 (FIG. 8). MS calcd for C12H17O5P 272.23, found 272.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with sodium bicarbonate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-925770571f2346f2ae8b46773068625f
Source dataset
uspto-grants-2013_05
Patent number
US08445706B2

Reaction notes

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