Methanol → HCID 22602995, compound

HRID 2307931Notes

Reaction equation

HRID 2307931 reaction equation
O[C:2]1[CH:16]=[C:15]([CH3:17])[C:5]([CH2:6][C:7]2[O:11][C:10](C(O)=O)=[CH:9][CH:8]=2)=[C:4]([CH3:18])[CH:3]=1.O[C:20]1[CH:34]=[C:33]([CH3:35])[CH:32]=[C:31]([CH3:36])[C:21]=1[CH2:22][C:23]1[O:27][C:26](C(O)=O)=[CH:25][CH:24]=1.[OH2:37].[C:38]1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:49][OH:50].[OH2:51]>C1(C)C=CC=CC=1>[CH3:38][O:37][C:2]1[CH:3]=[C:4]([CH3:18])[C:5]([CH2:6][C:7]2[O:50][C:49]([C:26]([O:27][CH3:23])=[O:51])=[CH:9][CH:8]=2)=[C:15]([CH3:17])[CH:16]=1.[CH3:38][O:37][C:20]1[CH:34]=[C:33]([CH3:35])[CH:32]=[C:31]([CH3:36])[C:21]=1[CH2:22][C:23]1[O:50][C:49]([C:10]([O:11][CH3:7])=[O:51])=[CH:25][CH:24]=1

Participants

8

Reactant 5

HCID 887MethanolHCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 22602998HCID 22602998, compoundHCID 22603012HCID 22603012, compound

Product 2

HCID 22602995HCID 22602995, compoundYield 100%HCID 22603014HCID 22603014, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

In a 500-mL round-bottom flask, a mixture of 5-(4-hydroxy-2,6-dimethylbenzyl)-2-furoic acid (200) and 5-(2-hydroxy-4,6-dimethylbenzyl)-2-furoic acid (201) (4.28 g, 17.38 mmol) and toluene (40 mL) were placed. To this solution p-toluenesulfonic acid monohydrate (3.31 g, 17.38 mmol) and methanol (10 mL, 246.87 mmol) were added. The reaction mixture was heated to 100° C. overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The separated organic layer was washed with brine, dried over MgSO4, and concentrated to yield methyl 5-(4-methoxy-2,6-dimethylbenzyl)-2-furoate (202) and methyl 5-(2-methoxy-4,6-dimethylbenzyl)-2-furoate (203) (4.52 g, 100% yield).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe separated organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bd95b90dc36043d3a1a231c3de0e06c9
Source dataset
uspto-grants-2004_12
Patent number
US06833372B2

Reaction notes

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