Hydrochloric Acid → HCID 23134875, compound

HRID 1437838Notes

Reaction equation

HRID 1437838 reaction equation
[Cl:1][C:2]1[C:3]([OH:11])=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH:12](=[O:24])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[Cl-].[Ca+2].[Cl-].CO.[OH-].[K+].Cl>CO>[Cl:1][C:2]1[C:3]([OH:11])=[C:4]([CH:12]([OH:24])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[Cl:1][C:2]1[C:3]([OH:11])=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8194DodecanalHCID 5284359Calcium ChlorideHCID 147660725-chloro-2,4-dihydroxybenzaldehydeHCID 23689386Potassium hydroxide methanol

Product 2

HCID 147660725-chloro-2,4-dihydroxybenzaldehydeYield 42%HCID 23134875HCID 23134875, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Chloro-2,4-dihydroxybenzaldehyde (493 mg, 2.86 mmol), dodecanal (641 mg, 3.48 mmol) and calcium chloride dehydrate (3.02 mg, 2.03 mmol) were dissolved in methanol (6 ml), added with a potassium hydroxide methanol solution (1.0 M, 4.0 ml) at 0° C. and stirred for 24 hours. The reaction mixture was made acidic with 1 M hydrochloric acid and extracted with ethyl acetate, and after post-treatment, the crude product (1.18 g) was purified by silica gel column chromatography (hexane:ethyl acetate=7:1) to obtain 5-chloro-2,4-dihydroxy-3-(1-hydroxydodecyl)benzaldehyde (colorless solid 475 mg, yield 46%) and 5-chloro-2,4-dihydroxybenzaldehyde (209 mg, recovery 42%).

Workup

  1. extractionextracted with ethyl acetate
  2. customafter post-treatment, the crude product (1.18 g) was purified by silica gel column chromatography (hexane:ethyl acetate=7:1)

Sources & evidence

ORD record
ord-99379ebf63c148d798977d5738404098
Source dataset
uspto-grants-2009_11
Patent number
US07622598B2

Reaction notes

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