Hydrochloric Acid → HCID 23134897, compound

HRID 1437837Notes

Reaction equation

HRID 1437837 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH:11](=[O:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[Cl-].[Ca+2].[Cl-].CO.[OH-].[K+].Cl>CO>[OH:1][C:2]1[C:9]([CH:11]([OH:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 72132,4-DihydroxybenzaldehydeHCID 8194DodecanalHCID 5284359Calcium ChlorideHCID 23689386Potassium hydroxide methanol

Product 2

HCID 72132,4-DihydroxybenzaldehydeYield 40%HCID 23134897HCID 23134897, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,4-Dihydroxybenzaldehyde (1.39 g, 10.0 mmol), dodecanal (2.21 g, 12.0 mmol) and calcium chloride dehydrate (1.03 g, 7.0 mmol) were dissolved in methanol (21 ml), added with a potassium hydroxide methanol solution (1.0 M, 14 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 (2.84 g) was purified by silica gel column chromatograophy (hexane:ethyl acetate=5:1) to obtain 2,4-dihydroxy-3-(1-hydroxy-dodecyl)benzaldehyde (colorless solid 1.65 g, yield 51%) and 2,4-dihydroxybenzaldehyde (552 mg, recovery 40%).

Workup

  1. extractionextracted with ethyl acetate
  2. customafter post-treatment, the crude product (2.84 g) was purified by silica gel column chromatograophy (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-974cf10b49e549a69b57ff183f8a9fd8
Source dataset
uspto-grants-2009_11
Patent number
US07622598B2

Reaction notes

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