Hydrochloric Acid → HCID 67791828, compound

HRID 2260164Notes

Reaction equation

HRID 2260164 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][CH:12]([OH:27])[C:13]2[CH:22]=[CH:21][C:20]3[C:19]([CH3:24])([CH3:23])[CH2:18][CH2:17][C:16]([CH3:26])([CH3:25])[C:15]=3[CH:14]=2)[CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].N1[CH:33]=[CH:32]C=CC=1.[C:34](Cl)(=[O:36])[CH3:35].Cl.[OH2:39]>>[C:34]([O:5][CH2:4][C:3]1[CH:6]=[CH:7][C:8]([O:10][CH2:11][CH:12]([OH:27])[C:13]2[CH:22]=[CH:21][C:20]3[C:19]([CH3:23])([CH3:24])[CH2:18][CH2:17][C:16]([CH3:26])([CH3:25])[C:15]=3[CH:14]=2)=[CH:9][C:2]=1[O:1][C:32](=[O:39])[CH3:33])(=[O:36])[CH3:35]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 1049PyridineHCID 6367Acetyl chlorideHCID 54301022HCID 54301022, compound

Product 1

HCID 67791828HCID 67791828, compound

Conditions

Temperature
0 °C

Procedure

1.2 g (3.23 mmol) of 2-hydroxy-4-[2-hydroxy-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2naphthyl)ethoxy]benzyl alcohol and 30 ml of pyridine are introduced into a flask and 345 ml (4.84 mmol) of acetyl chloride are added. The reaction mixture is stirred at 0° C. for 4 hours. It is poured into water, acidified with hydrochloric acid and extracted with ethyl acetate. The extract is washed with water, and the organic phase is separated, dried over sodium sulphate and evaporated. The residue obtained is purified by chromatography on a silica column, eluted with a mixture of hexane and ethyl acetate (70:30). After evaporation of the solvents, 140 mg (10.4%) of the expected product are collected in the form of a pale yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed with water
  3. customthe organic phase is separated
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a silica column
  8. washeluted with a mixture of hexane and ethyl acetate (70:30)
  9. customAfter evaporation of the solvents, 140 mg (10.4%) of the expected product
  10. customare collected in the form of a pale yellow oil

Sources & evidence

ORD record
ord-5c52acadcf2847e3a2d44f189d4e5af9
Source dataset
uspto-grants-1995_12
Patent number
US05476860

Reaction notes

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