Diethyl Ether → 4-[3-Hydroxy-3-methyl-1-(naphthalen-1-yl)butyl]benzene-1,3-diol

HRID 614751Notes

Reaction equation

HRID 614751 reaction equation
[CH3:1][Li].[OH:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]([C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[CH:17][CH:16]=3)[CH2:9]C(=O)[O:11]2)=[CH:6][CH:5]=1.CC[O:27][CH2:28][CH3:29]>>[OH:11][C:12]1[CH:13]=[C:4]([OH:3])[CH:5]=[CH:6][C:7]=1[CH:8]([C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1)[CH2:9][C:28]([CH3:29])([OH:27])[CH3:1]

Participants

4

Reactant 3

HCID 3283Diethyl Ether2×HCID 205705223,4-Dihydro-7-hydroxy-4-(1-naphthyl)coumarinHCID 178418348HCID 178418348, compound

Product 1

HCID 205705454-[3-Hydroxy-3-methyl-1-(naphthalen-1-yl)butyl]benzene-1,3-diol

Procedure

To a stirred solution of methyl lithium in ether (80 ml, 1.9M solution) at ambient temperature under nitrogen was added portionwise over 0.5 hour finely divided 3,4-dihydro-7-hydroxy-4-(1-naphthyl)coumarin (7.52 g). The ether boiled during the addition and the solid material gradually dissolved. After the addition was complete the solution was boiled under reflux for 4 hours then cooled and poured into acid. The ether extract yielded 4-(2,4-dihydroxyphenyl)-2-methyl-4-(1-naphthyl)-2-butanol which was dissolved in glacial acetic acid (55 ml) and boiled under reflux overnight. The product was poured into water (200 ml) and extracted into ether. The ether extract was washed with water and aqueous sodium bicarbonate then dried (magnesium sulphate). Removal of the solvent gave the title compound (7.70 g) as a foam containing some ether.

Workup

  1. dissolutionthe solid material gradually dissolved
  2. additionAfter the addition
  3. temperatureunder reflux for 4 hours
  4. temperaturethen cooled
  5. additionpoured into acid
  6. extractionThe ether extract

Sources & evidence

ORD record
ord-349e733321c641d0bc3d564335888d1c
Source dataset
uspto-grants-1979_03
Patent number
US04146539

Reaction notes

Loading…