Hexane → 6-(Hydroxymethyl)-2-benzofuran-1(3H)-one

HRID 1766854Notes

Reaction equation

HRID 1766854 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O1CCCCC1O[CH2:20][C:21]1[CH:29]=[CH:28][C:27]([CH2:30][O:31]C2CCCCO2)=[CH:26][C:22]=1[C:23]([OH:25])=[O:24].C(OCC)(=O)C.CCCCCC>CO>[OH:31][CH2:30][C:27]1[CH:26]=[C:22]2[C:21]([CH2:20][O:24][C:23]2=[O:25])=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 211104372,5-Bis[(tetrahydropyran-2-yl)oxymethyl]benzoic acid

Product 1

HCID 178625846-(Hydroxymethyl)-2-benzofuran-1(3H)-oneYield 77.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

p-Toluenesulfonic acid monohydrate (103.0 mg, 0.54 mmol) was added to a solution of 2,5-bis[(tetrahydropyran-2-yl)oxymethyl]benzoic acid (1.62 g, 4.64 mmol) obtained from Example 1-(3) in methanol (30 ml), and the mixture was stirred at room temperature for 2 hours. The resulting solution was concentrated under reduced pressure to afford a solid residue. This residue was subjected to chromatography on a silica gel (50 g) column (eluent; ethyl acetate:hexane=1:1˜1:0) to give the title compound (587.5 mg, 77% yield) as a colorless solid (mp. 107-108° C.).

Workup

  1. concentrationThe resulting solution was concentrated under reduced pressure
  2. customto afford a solid residue

Sources & evidence

ORD record
ord-528eddc3c9074613b7c1a7c5b7738b3f
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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