Phosphoric Acid → HCID 74020148, compound

HRID 1437839Notes

Reaction equation

HRID 1437839 reaction equation
[Cl:1][C:2]1[C:3]([OH:24])=[C:4]([CH:11](O)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].P(=O)(O)(O)O.[Cl-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[C:3]([OH:24])=[C:4]([CH:11]=[CH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 5234Sodium ChlorideHCID 23134875HCID 23134875, compound

Product 1

HCID 74020148HCID 74020148, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Chloro-2,4-dihydroxy-3-(1-hydroxydodecyl) benzaldehyde (300 mg, 0.84 mmol) was stirred in acetic acid (2 ml) in the presence of 85% phosphoric acid (0.81 ml) at a reflux temperature for one hour. The reaction mixture was cooled to room temperature, added with a saturated sodium chloride solution (20 ml). After extractive workup with ethyl acetate, the crude product was purified by, silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 5-chloro-3-(1-dodecenyl)-2,4-dihydroxybenzaldehyde (pale yellow solid 238 mg, yield 84%)

Workup

  1. customAfter extractive workup with ethyl acetate, the crude product was purified by, silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-88f554f0fda844a091d58a023d9444e7
Source dataset
uspto-grants-2009_11
Patent number
US07622598B2

Reaction notes

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