Water → HCID 67546509, compound

HRID 2407475Notes

Reaction equation

HRID 2407475 reaction equation
P(=O)(O)(O)O.O.O[CH2:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[C:17]([OH:20])([CH3:19])[CH3:18])[C:12]#[N:13]>C1(C)C=CC=CC=1>[CH3:19][C:17]1([CH3:18])[C:16]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=2[CH2:8][O:20]1

Participants

5

Reactant 3

HCID 962WaterHCID 1004Phosphoric AcidHCID 67547071HCID 67547071, compound

Product 1

HCID 67546509HCID 67546509, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of orthophosphoric acid (147.5 mL) and demineralized water (29.5 mL) is added to a stirred toluene solution (300 mL) of 3-hydroxymethyl-4-(1-hydroxy-1-methylethyl)benzonitrile (29.5 g, 0.154 mol) at 0-5° C. The reaction mixture is stirred at room temperature for 3.0 hrs. The toluene layer is separated and the aqueous layer is extracted with toluene (3×50 mL). Combined organic layers are washed with saturated sodium bicarbonate solution (1×40 mL) followed by demineralized water (1×40 mL). Evaporation of the toluene layer under reduced pressure gives a viscous liquid which is purified by column chromatography (silica gel 230-400 mesh,) to give 1,1-dimethyl-1,3-dihydro-2-benzofuran-5-carbonitrile.

Workup

  1. customThe toluene layer is separated
  2. extractionthe aqueous layer is extracted with toluene (3×50 mL)
  3. washCombined organic layers are washed with saturated sodium bicarbonate solution (1×40 mL)
  4. customEvaporation of the toluene layer under reduced pressure
  5. customgives a viscous liquid which
  6. customis purified by column chromatography (silica gel 230-400 mesh,)

Sources & evidence

ORD record
ord-84ab4528269e44e8b5d0b46299bb3192
Source dataset
uspto-grants-2014_08
Patent number
US08809539B2

Reaction notes

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