Water → HCID 86746180, compound

HRID 465736Notes

Reaction equation

HRID 465736 reaction equation
[CH3:1][C:2]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH:20]2[O:22][CH2:21]2)=[CH:14][CH:13]=1)([CH3:11])[CH2:3][O:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1.[CH3:23][O:24][C:25](=[O:33])[C:26]1C=CC(O)=[CH:28][CH:27]=1.[Na].C[O:36][C:37](=O)[C:38]1C=CC(O)=C[CH:39]=1.O>CN(C)C=O.C(OCC)(=O)C>[CH3:23][O:24][C:25](=[O:33])[C:26]1[CH:27]=[CH:28][C:18]([C:15]2[CH:14]=[CH:13][C:12]([C:2]([CH3:11])([CH3:1])[CH2:3][O:4][CH:5]3[CH2:10][CH2:9][CH2:8][CH2:7][O:6]3)=[CH:17][CH:16]=2)=[CH:19][C:20]=1[O:22][CH2:21][CH:37]([OH:36])[CH2:38][CH3:39]

Participants

7

Reactant 4

HCID 962WaterHCID 7456MethylparabenHCID 19875584HCID 19875584, compoundHCID 665884945026-62-0

Product 1

HCID 86746180HCID 86746180, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

30.4 g (0.100 Mol) 4-{4'-[1,1-dimethyl-2-(tetrahydropyran-2-yl)oxyethyl]phenyl}-1,2-epoxy butane, 15.2 g (0.100 Mol) 4-hydroxybenzoic acid methyl ester and 1.74 g (0.010 Mol) 4-hydroxy benzoic acid methyl ester sodium salt are heated in 100 ml dimethyl formamide for 23 hours while stirring to 100°-110° C. The cooled reaction mixture is poured into water, the precipitating product taken up in ethyl acetate and the organic phase washed with water. After drying over sodium sulfate the solvent is removed in vacuum and the residue chromatographed on silica with dichloromethane/methanol 99/1. A highly viscous oil is obtained; yield 32.5 g (71%).

Workup

  1. customThe cooled reaction mixture
  2. washthe organic phase washed with water
  3. dry with materialAfter drying over sodium sulfate the solvent
  4. customis removed in vacuum
  5. customthe residue chromatographed on silica with dichloromethane/methanol 99/1
  6. customA highly viscous oil is obtained

Sources & evidence

ORD record
ord-4a925d69b19e46498d5cc2a2c6f29799
Source dataset
uspto-grants-1992_10
Patent number
US05153353

Reaction notes

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