Hydrochloric Acid → 2,4-Dihydroxy-3-(1-hydroxydodecyl)-6-methylbenzaldehyde

HRID 1437832Notes

Reaction equation

HRID 1437832 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([CH3:11])[C:3]=1[CH:4]=[O:5].[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].O.O.[Cl-].[Ca+2].[Cl-].CO.[OH-].[K+].Cl>>[OH:1][C:2]1[C:9]([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:8]([OH:10])[CH:7]=[C:6]([CH3:11])[C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8194DodecanalHCID 251690o-OrsellinaldehydeHCID 6093260Calcium chloride, dihydrateHCID 23689386Potassium hydroxide methanol

Product 1

HCID 117720542,4-Dihydroxy-3-(1-hydroxydodecyl)-6-methylbenzaldehydeYield 28.7%

Procedure

2,4-Dihydroxy-6-methylbenzaldehyde (91 mg, 0.60 mmol) described in M. M. Joullie et al., J. Org. Chem., 50, 3997 (1985), dodecanal (133 mg, 0.72 mmol) and calcium chloride dihydrate (59 mg, 0.40 mmol) were stirred in a 0.4 M potassium hydroxide methanol solution (2 ml) at 0° C. for 24 hours. The reaction mixture was made acidic with 1 M hydrochloric acid. After extractive workup with ethyl acetate, the crude product was purified by silica gel thin-layer chromatography (hexane:ethyl acetate=3:1) to obtain 2,4-dihydroxy-3-(1-hydroxydodecyl)-6-methylbenzaldehyde (58 mg, yield 28%).

Workup

  1. customAfter extractive workup with ethyl acetate, the crude product was purified by silica gel thin-layer chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-d0d4a35e015a466497e96d08160ba9d1
Source dataset
uspto-grants-2009_11
Patent number
US07622598B2

Reaction notes

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