Hydrochloric Acid → 3,5-Diacetoxy-4'-hydroxy stilbene

HRID 78874Notes

Reaction equation

HRID 78874 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:15]=[CH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23]C(=O)CCl)=[CH:19][CH:18]=2)[CH:8]=[C:9]([O:11][C:12](=[O:14])[CH3:13])[CH:10]=1)(=[O:3])[CH3:2].Cl>N1C=CC=CC=1>[C:12]([O:11][C:9]1[CH:8]=[C:7]([CH:15]=[CH:16][C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH:6]=[C:5]([O:4][C:1](=[O:3])[CH3:2])[CH:10]=1)(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 722512213,5-Diacetoxy-4'-chloroacetoxy stilbene

Product 1

HCID 4058513,5-Diacetoxy-4'-hydroxy stilbeneYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3,5-diacetoxy-4′-chloroacetoxy stilbene (0.388 g, 1 mmol) in 50% aqueous pyridine, which was adjusted to pH 6.7 with hydrochloric acid, was stirred for 6 h at room temperature. The mixture was concentrated and diluted with EtOAc. The mixture was washed with 1 N aqueous HCl, saturated NaHCO3 and water. Then the EtOAc solution was dried and concentrated. After purification by radial chromatography, the product (0.28 g, 90%) was obtained. Data are: 1H NMR (Aceton-d6, 300 MHz) δ 8.55 (bs, 1H), 7.47 (m, 2H), 7.25-7.00 (m, 4H), 6.86 (m, 2H), 6.82 (t, 1H, J=2.1 Hz), 2.27 (s, 3H); 13C NMR (Aceton-d6, 75 MHz) δ169.5, 158.7, 152.7, 141.2, 131.4, 129.5, 129.2, 124.8, 117.5, 116.6, 115.1, 21.0; HRMS (EI+) found 312.0993 M+, calcd 312.0998 for C18H16O6.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with EtOAc
  3. washThe mixture was washed with 1 N aqueous HCl, saturated NaHCO3 and water
  4. dry with materialThen the EtOAc solution was dried
  5. concentrationconcentrated
  6. customAfter purification by radial chromatography

Sources & evidence

ORD record
ord-f82eabb860cd4ad7b06e86f12fedb944
Source dataset
uspto-grants-2014_09
Patent number
US08841477B2

Reaction notes

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