Isobutanol → 6-Hydroxy-5-isobutoxymethyl-3,4-dihydro-2H-naphthalen-1-one

HRID 496400Notes

Reaction equation

HRID 496400 reaction equation
Cl[CH2:2][C:3]1[C:12]([OH:13])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:14].C(N(CC)CC)C.[CH2:22]([OH:26])[CH:23]([CH3:25])[CH3:24]>>[OH:13][C:12]1[C:3]([CH2:2][O:26][CH2:22][CH:23]([CH3:25])[CH3:24])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:14])[CH2:7][CH2:6][CH2:5]2

Participants

4

Reactant 3

HCID 6560IsobutanolHCID 8471TriethylamineHCID 123936195-(chloromethyl)-6-hydroxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 223247596-Hydroxy-5-isobutoxymethyl-3,4-dihydro-2H-naphthalen-1-one

Conditions

Temperature
108 °C

Procedure

To a solution of 5-Chloromethyl-6-hydroxy-3,4-dihydro-2H-naphthalen-1-one, prepared as described Chem. Pharm. Bull. 25(11)2988-3002(1077), (0.211 g, 0.001 mol) and triethylamine (0.167 ml, 0.0012 mol, Mallinckrodt) contained in a 16×125 mm screw top glass tube, was added isobutyl alcohol (3 ml, Aldrich Chemical). The tube was capped with a teflon lined cap and placed on an orbital mixing heat block at reflux temperature (˜108° C.) for 16 hrs. The reaction mixture was concentrated in vacuo to a pink-red syrup. On addition of ethyl ether, a pinkish solid precipitated from the syrup. Washed mixture with 5% citric acid, brine, and dried organic phase over anhydrous sodium sulfate. Evaporated mixture in vacuo to yield a red-pink powder, 0.210 g, 85% crude yield. Low resolution mass spectroscopy (APCI) 249 [M+H]+.

Workup

  1. customlined cap
  2. additionmixing
  3. temperatureheat block
  4. concentrationThe reaction mixture was concentrated in vacuo to a pink-red syrup
  5. additionOn addition of ethyl ether
  6. customa pinkish solid precipitated from the syrup
  7. washWashed mixture with 5% citric acid, brine, and dried organic phase over anhydrous sodium sulfate
  8. customEvaporated mixture in vacuo
  9. customto yield a red-pink powder, 0.210 g, 85% crude yield

Sources & evidence

ORD record
ord-b0bae762cd17464f9479998fef47029e
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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