Water → HCID 10307943, compound

HRID 480977Notes

Reaction equation

HRID 480977 reaction equation
[CH3:1][C:2]1[C:13]([O:14]C2CCCCO2)=[CH:12][C:5]2[CH:6]=[C:7]([C:9](=[O:11])[CH3:10])[O:8][C:4]=2[C:3]=1[CH3:21].OC1C(C)=C(C)C(O)=CC=1C=O.O>Cl.CO>[OH:14][C:13]1[C:2]([CH3:1])=[C:3]([CH3:21])[C:4]2[O:8][C:7]([C:9](=[O:11])[CH3:10])=[CH:6][C:5]=2[CH:12]=1

Participants

6

Reactant 3

HCID 962WaterHCID 22026140HCID 22026140, compoundHCID 22026144HCID 22026144, compound

Product 1

HCID 10307943HCID 10307943, compoundYield 62.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-[6,7-dimethyl-5-(tetrahydro-pyran-2-yloxy)-benzofuran-2-yl]-ethanone (1.1 g) (prepared from 2,5-dihydroxy-3,4-dimethyl-benzaldehyde following the procedure of Steps 3, 4 and 5 of Example 13) and conc. HCl (10 drops) in MeOH (20 mL) was stirred at room temperature for 2 h. Water was poured into the mixture and left to precipitate overnight in the refrigerator. The precipitate was collected, washed with hexane and dried to give 1-(5-hydroxy-6,7-dimethyl-benzofuran-2-yl)-ethanone as a light brown solid (490 mg). 1H NMR (CDCl3, 300 MHz) δ: 7.38 (s, 1H), 6.89 (s, 1H), 4.88 (1H, OH), 2.60, 2.50, 2.31 (3s, 9H) ppm. 13C NMR (CDCl3, 75 MHz) δ: 192.76, 155.45, 155.13, 153.72, 130.29, 127.27, 124.75, 117.44, 106.18, 29.30, 15.56, 15.28 ppm. MS (m/z): 205 (M+H+).

Workup

  1. waitleft
  2. customto precipitate overnight in the refrigerator
  3. customThe precipitate was collected
  4. washwashed with hexane
  5. customdried

Sources & evidence

ORD record
ord-d3511f78e8f84606a949f59daae628a9
Source dataset
uspto-grants-2003_11
Patent number
US06653346B1

Reaction notes

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