4-Hydroxybenzaldehyde → HCID 13463483, compound

HRID 2372666Notes

Reaction equation

HRID 2372666 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH3:16][C@@H:17]([CH2:31][CH3:32])[CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=1.O[C:34]1[CH:41]=[CH:40][C:37]([CH:38]=[O:39])=[CH:36][CH:35]=1>CN(C)C1C=CN=CC=1.ClCCl>[CH:38]([C:37]1[CH:40]=[CH:41][C:34]([O:27][C:26](=[O:28])[C:25]2[CH:24]=[CH:23][C:22]([O:21][CH2:20][CH2:19][CH2:18][C@@H:17]([CH3:16])[CH2:31][CH3:32])=[CH:30][CH:29]=2)=[CH:35][CH:36]=1)=[O:39]

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 10868DicyclohexylcarbodiimideHCID 13463452HCID 13463452, compound

Product 1

HCID 13463483HCID 13463483, compoundYield 85.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3.7 g of N,N'-dicyclohexylcarbodiimide were added portionwise at 0° C. while stirring to a solution of 3.4 g of (S)-p-(4-methylhexyloxy)benzoic acid, 1.76 g of p-hydroxybenzaldehyde and 0.15 g of 4-(dimethylamino)-pyridine in 100 ml of dichloromethane. The mixture was stirred at 0° C. for a further 1 hour and at room temperature for 2 hours, then filtered and the filtrate was washed with 2N sodium carbonate solution and then with water, dried over sodium sulphate and concentrated. Chromatography of the residue on 120 g of silica gel with hexane/ethyl acetate (vol. 9:1) gave 4.2 g of pure (S)-p-(4-methylhexyloxy)benzoic acid p-formylphenyl ester.

Workup

  1. filtrationfiltered
  2. washthe filtrate was washed with 2N sodium carbonate solution
  3. dry with materialwith water, dried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c89a9647897d4938b7eda24e08c133ab
Source dataset
uspto-grants-1992_03
Patent number
US05100577

Reaction notes

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