2,2-Dimethoxypropane → HCID 21993607, compound

HRID 2251728Notes

Reaction equation

HRID 2251728 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH2:11][OH:12])[CH:6]=[CH:7][C:8]=1[CH2:9][OH:10].CO[C:15](OC)([CH3:17])[CH3:16]>C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:16][C:15]1([CH3:17])[O:1][CH2:2][C:3]2[CH:4]=[C:5]([CH2:11][OH:12])[CH:6]=[CH:7][C:8]=2[CH2:9][O:10]1

Participants

4

Reactant 2

HCID 64952,2-DimethoxypropaneHCID 114692971,2,4-Benzenetrimethanol

Product 1

HCID 21993607HCID 21993607, compoundYield 14,357.5%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

5 g of (3,4-bis-hydroxymethylphenyl)methanol (29.7 mmol), 25 ml of 2,2-dimethoxypropane (21.2 g; 0.2 mmol) and 0.29 g of p-toluenesulfonic acid (1.5 mmol) are introduced into a flask. After stirring for 1 hour 10 minutes at room temperature, the solvent is evaporated under vacuum at 30° C. and the crude product is chromatographed on silica gel (dichloromethane/methanol/aqueous ammonia=98/2/0.1). 5.98 g of (7,7-dimethyl-(5H,9H)-6,8-dioxabenzocyclohepten-2-yl)methanol are obtained in the form of a white powder.

Workup

  1. customthe solvent is evaporated under vacuum at 30° C.
  2. customthe crude product is chromatographed on silica gel (dichloromethane/methanol/aqueous ammonia=98/2/0.1)

Sources & evidence

ORD record
ord-dfe53bb01583456f9cd24ebbdab620d1
Source dataset
uspto-grants-2008_01
Patent number
US07319155B2

Reaction notes

Loading…