Phosphoric Acid → HCID 22868491, compound

HRID 1275033Notes

Reaction equation

HRID 1275033 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][O:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]([O:18][CH3:19])[C:11]=1[C@@H:20]1[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]1[OH:26].P(=O)(O)(O)O.C[O:33][C:34]1C=CC(C=O)=C[CH:39]=1>ClCCl>[C:1]([O:26][C@@H:21]1[CH2:22][CH2:23][CH2:24][CH2:25][C@H:20]1[C:11]1[C:12]([O:18][CH3:19])=[CH:13][C:14]([O:16][CH3:17])=[C:15]([C:34](=[O:33])[CH3:39])[C:10]=1[O:9][CH3:8])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 1004Phosphoric AcidHCID 7918Acetic AnhydrideHCID 312444-MethoxybenzaldehydeHCID 12043059HCID 12043059, compound

Product 1

HCID 22868491HCID 22868491, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (660 ml; 6.975 mol) was added to the solution of the trans-(+/-)-2-(2,4,6-trimethoxyphenyl)cyclohexanol (II; 60 g; 0.225 mol) in dichloromethane (300 ml) at room temperature, while stirring. It was followed by the dropwise addition of orthophosphoric acid (85%; 40 ml; 0.347 mol) over 45 min. Reaction progress was monitored by TLC (tlc system 30% ethyl acetate-pet ether; spray reagent--anisaldehyde; product Rf--value=0.5). TLC of the reaction mixture after 15 min. revealed complete consumption of the starting material. The reaction mixture was then diluted with 250 ml of cold water, neutralized with solid sodium bicarbonate and extracted with dichloromethane (3×500 ml). The combined organic layer was washed with bicarbonate solution, water, brine and dried over sodium sulphate. It was then concentrated in-vacuo and the residue chromatographed over silica gel (column diam. 9.0 cm; silica gel--1 kg; eluent--5% and 10% ethyl acetate-pet ether) to get the title compound (64 gm; yield 81%; m.p. 82-85° C.).

Workup

  1. customReaction progress
  2. customconsumption of the starting material
  3. additionThe reaction mixture was then diluted with 250 ml of cold water
  4. extractionextracted with dichloromethane (3×500 ml)
  5. washThe combined organic layer was washed with bicarbonate solution, water, brine
  6. dry with materialdried over sodium sulphate
  7. concentrationIt was then concentrated in-vacuo
  8. customthe residue chromatographed over silica gel (column diam. 9.0 cm; silica gel--1 kg; eluent--5% and 10% ethyl acetate-pet ether)

Sources & evidence

ORD record
ord-5ea9ddff49364f489042ef14f72a1a52
Source dataset
uspto-grants-2000_12
Patent number
US06159988

Reaction notes

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