4-Bromoanisole → HCID 19387414, compound

HRID 2399272Notes

Reaction equation

HRID 2399272 reaction equation
[CH2:1]([C:8]1[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=1[C:10]([O:12]C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([Mg]Br)=[CH:22][CH:21]=1.[Mg].Br[C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1>C1COCC1>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:10]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)([C:9]2[CH:14]=[CH:15][CH:16]=[CH:17][C:8]=2[CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[OH:12])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 77304-BromoanisoleHCID 2357306962-60-3HCID 5462224MagnesiumHCID 178491912HCID 178491912, compound

Product 1

HCID 19387414HCID 19387414, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-benzylbenzoate (10.0 g) was added dropwise to a stirred solution of 4-methoxyphenyl magnesium bromide, which was prepared in situ from magnesium (3.2 g) and 4-bromoanisole (24.9 g), in THF at room temperature. After 16 hours, the mixture was quenched with ammonium chloride solution and the solvent evaporated in vacuoo The residue was extracted with ethyl acetate, dried (MgSO4), filtered, and evaporated in vacuo to give di-(4-methoxyphenyl)-(2-benzylphenyl)carbinol as an oil. This oil was dissolved in acetic acid (50 mL) and concentrated H2SO4 (2.0 mL) was added the resulting mixture was heated to 100° C. for one hour and then neutralized with NaOH solution. The mixture was extracted with ether and the organic extracts were combined, dried (MgSO4), filtered, evaporated in vacuo and chromatographed on silica gel eluting with hexane/ethyl acetate (10/1) to give 9,9-bis(4-methoxyphenyl)-(9H, 10H)-dihydroanthracene (7.1 g) as a solid. M.P. 138°-140° C. Demethylation was performed using the sodium ethanethiolate/DMF procedure described in Example 3 to give the title product in 77% yield as a solid. M.P. 230°-232° C.

Workup

  1. customthe mixture was quenched with ammonium chloride solution
  2. customthe solvent evaporated in vacuoo The residue
  3. extractionwas extracted with ethyl acetate
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-63cea2e6fbe74ff584c07e82fb4e826f
Source dataset
uspto-grants-1995_09
Patent number
US05447960

Reaction notes

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